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  • 50-02-2 Structure
  • Basic information

    1. Product Name: Dexamethasone
    2. Synonyms: 16alpha)-;16alpha)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-(11bet;16alpha-methyl-9alpha-fluoro-1,4-pregnadiene-11beta,17alpha,21-triol-2,20-dione;16-alpha-methyl-9-alpha-fluoro-1,4-pregnadiene-11-beta,17-alpha,21-triol-3,2;16-alpha-Methyl-9-alpha-fluoro-1,4-pregnadiene-11-beta,17-alpha,21-triol-3,20-dione;16-alpha-methyl-9-alpha-fluoro-11-beta,17-alpha,21-trihydroxypregna-1,4-dien;16alpha-Methyl-9alpha-fluoro-11beta-17alpha-21-trihydroxypregna-1,4-diene-3,20-dione;16-alpha-methyl-9-alpha-fluoro-1-dehydrocortisol
    3. CAS NO:50-02-2
    4. Molecular Formula: C22H29FO5
    5. Molecular Weight: 392.46
    6. EINECS: 200-003-9
    7. Product Categories: Active Pharmaceutical Ingredients;Antitumors for Research and Experimental Use;Biochemistry;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds;Steroid and Hormone;Pharmaceutical intermediate;API;MAXIDEX;Hormone Drugs;Mainly used for anti-inflammatory and allergy;Pharmaceutical intermediates;pharmaceutical intermediate and medicine grade
    8. Mol File: 50-02-2.mol
    9. Article Data: 31
  • Chemical Properties

    1. Melting Point: 262-264 °C(lit.)
    2. Boiling Point: 568.2 °C at 760 mmHg
    3. Flash Point: 9℃
    4. Appearance: off-white/powder
    5. Density: 1.1283 (estimate)
    6. Vapor Pressure: 2.81E-15mmHg at 25°C
    7. Refractive Index: 76 ° (C=1, Dioxane)
    8. Storage Temp.: 2-8°C
    9. Solubility: ethanol: 1 mg/mL
    10. PKA: 12.13±0.70(Predicted)
    11. Water Solubility: 10 mg/100 mL (25 ºC)
    12. Sensitive: Light Sensitive
    13. Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, acid anhydrides, acid chlorides. May be light sens
    14. Merck: 14,2943
    15. BRN: 2066651
    16. CAS DataBase Reference: Dexamethasone(CAS DataBase Reference)
    17. NIST Chemistry Reference: Dexamethasone(50-02-2)
    18. EPA Substance Registry System: Dexamethasone(50-02-2)
  • Safety Data

    1. Hazard Codes: Xi,Xn,T,F
    2. Statements: 43-40-36/37/38-20/21/22-42/43-39/23/24/25-23/24/25-11
    3. Safety Statements: 36/37-45-36-26-22-16
    4. RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
    5. WGK Germany: 2
    6. RTECS: TU3980000
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 50-02-2(Hazardous Substances Data)

50-02-2 Usage

Description

Dexamethasone is an anti-inflammatory glucocorticoid, chemically known as 9-fluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione, and is the 16-isomer of betamethasone. It is an odorless white to off-white crystalline powder with a slightly bitter taste. Dexamethasone is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is also useful for studying apoptosis, cell signaling pathways, and gene expression. Additionally, it is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine.

Uses

Used in Medical Applications:
Dexamethasone is used as a glucocorticoid for treating various conditions, including circulatory collapse, shock during or after surgical operations, trauma, blood loss, myocardial infarction, and burns. It is also used in severe infections such as toxemia, vascular collapse in meningococcosis, septicemia, diphtheria, typhoid fever, and peritonitis.
Used in Allergic Conditions:
Dexamethasone is used as an anti-inflammatory glucocorticoid for treating severe allergic conditions, including asthmatic status, laryngeal edema, severe anaphylactic reactions to medicinal drugs, and pyrogenic reactions.
Used in Inflammatory and Autoimmune Conditions:
Dexamethasone is used as an anti-inflammatory glucocorticoid for treating inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm.
Used in Veterinary Medicine:
Dexamethasone is used in combination with trichlormethiazide to treat horses with swelling of distal limbs and general bruising. It is also associated with marbofloxacin and clotrimazole to treat difficult ear infections in dogs.
Used in Research:
Dexamethasone is used to study apoptosis, cell signaling pathways, and gene expression due to its various biological activities, such as inducing the production of phospholipase A2 inhibitory protein (lipocortin), inhibiting the induction of nitric oxide synthase, and regulating T cell survival, growth, and differentiation.
Chemical Properties:
Dexamethasone is a white or almost white, crystalline powder.
Brand Names:
Aeroseb-Dex (Allergan), Decadron (Merck), Dexone (Solvay Pharmaceuticals), Hexadrol (Organon), Maxidex (Alcon), Mymethasone (Morton Grove).

Anti-inflammatory effects

Dexamethasone reduces and prevents the tissue response to inflammation, thereby reducing the manifestations of inflammation. Hormones inhibit the accumulation of inflammatory cells, including macrophages and leukocytes, at sites of inflammation, and inhibit phagocytosis, the release of lysosomal enzymes, and the synthesis and release of inflammatory chemical mediators.

Side Effects

Dexamethasone is a artificially synthetic glucocorticoid, belonging to a long-term glucocorticoid drugs. Glucocorticoids can promote the metabolism of the three major nutrients while preventing protein synthesis with long-term topical being able to causing more serious consequences. However, the adverse effects should be much smaller than oral medication. Common side effects of systemic corticosteroid include: It can cause stomach discomfort and increased sensitivity to stomach ulcers. It can Increase the appetite and results in a significant increase in body weight. Potential patients with diabetes: glucose intolerance in patients with aggravating existing diabetes. It can cause mental illness including personality changes, irritability, agitation, and mania. It can be used for the long-term treatment of osteoporosis: pathological fractures (such as hip). It can cause elevated liver enzymes, fatty liver degeneration (usually reversible). For patients of nephrotic syndrome, applying long-term high-dose medication is likely to cause large side effects such as gastrointestinal ulcers and avascular necrosis. For treatment of nephrotic syndrome, it is better to apply prednisone acetate tablets. Dexamethasone can be used for the treatment of high altitude cerebral edema and pulmonary edema. Upon climbing expeditions, people can apply it to alleviate altitude sickness. Combination with marbofloxacin and clotrimazole, etc. can be used for treating the ear infection and allergies of a dog or a bird. The above information is edited by the lookchem of Dai Xiongfeng.

Drug Reactions

Dexamethasone is a corticosteroid known as a glucocorticoid. Corticosteroids are meant to resemble a naturally occurring hormone produced in the adrenal cortex, cortisol. Corticosteroids act on the immune system by blocking the production of substances that trigger inflammatory and immune responses. Dexamethasone may react with these drugs: Amphotericin Aspirin Cyclophosphamide Cyclosporine Digoxin Daunorubicin HCl Doxorubicin HCl Insulin Mitotane Phenobarbital Phenytoin sodium Rifampin Rimadyl

Indications

Cushing’s disease is defined as hypercortisolism due to chronic overproduction of corticotrophin by a corticotroph adenoma. Cortisol’s lack of suppressibility during the administration of low doses of dexamethasone but suppressibility during high-dose dexamethasone is the key diagnostic finding in 99% of the patients with Cushing’s disease. This contrasts with the lack of glucocorticoid suppressibility typically found in patients with corticotrophin-independent hypercortisolism (Cushing’s syndrome). A judicious selection of the available tests may be necessary to obtain an accurate diagnosis in patients with Cushing’s syndrome.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Dexamethasone may be sensitive to prolonged exposure to light. Dexamethasone is incompatible with strong oxidizers, strong acids, acid chlorides and acid anhydrides. Oxidation may occur with bases.

Fire Hazard

Flash point data for Dexamethasone are not available; however, Dexamethasone is probably combustible.

Biological Activity

Glucocorticoid; anti-inflammatory. Reduces levels of activated NF- κ B in immature dendritic cells (DCs) and inhibits differentiation into mature DCs.

Biochem/physiol Actions

Target IC50: 5 nM Inhibiting the expression of inducible but not constitutive nitric oxide synthase in vascular endothelial cells

Pharmacology

Dexamethasone is a corticosteroid with high glucocorticoid activity and virtually no mineralocorticoid activity. I ts mechanism of action as an antiemetic is unknown, but it is possible that either direct genomic or indirect non-genomic effects on 5-HT3 and GABAA receptors contribute to its antiemetic activity. Many of the original studies were carried out using 8– 10mg of dexamethasone phosphate, but smaller doses (2.5–4mg) provide equal antiemetic efficacy with minimal risk of adverse effects. Concerns relating to adrenal suppression and other steroid-induced adverse effects (including increased risk of bleeding) after a single dose of dexamethasone remain largely unfounded. O ne of the most unpleasant adverse effects of dexamethasone involves intense perineal stimulation after rapid i.v. injection.

Pharmacokinetics

The activity of dexamethasone, as measured by glycogen deposition, is 20 times greater than that of hydrocortisone. It has five times the anti-inflammatory activity of prednisolone. Clinical data indicate that this compound has seven times the antirheumatic potency of prednisolone. It is roughly 30 times more potent than hydrocortisone. Its pharmacokinetics are presented in Table 33.3. Routes of metabolism for dexamethasone are similar to those for prednisolone, with its primary 6β-hydroxy metabolite being recovered in urine. Dexamethasone sodium phosphate is the water-soluble sodium salt of the 21-phosphate ester, with an IV half-life of less than 10 minutes because of rapid hydrolysis by plasma phosphatases. Peak plasma levels for dexamethasone usually are attained in approximately 10 to 20 minutes following its IV administered dose. A similar reaction occurs when the phosphate ester is applied topically or by inhalation.

Clinical Use

Corticosteroid:Cerebral oedemaBacterial meningitis (unlicensed indication)Suppression of inflammatory and allergic disordersRheumatic diseaseCongenital adrenal hyperplasiaAnti-emetic (unlicensed indication)

Safety Profile

Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of F-.

Synthesis

Dexamethasone, 9α-fluoro-16α-methyl-11β,17,21-trihydroxypregna- 1,4-dien-3,20-dione (27.1.51), or simply 9α-fluoro-16α-methylprednisolone. The distinctive characteristic of dexamethasone is the presence of a fluorine atom at C9 of the steroid ring. Dexamethasone is synthesized in a multistage process from 3α-acetoxy-16-pregnen- 11,20-dione, which is reacted with methylmagnesium bromide in the presence of lithium bromide to give 3α-hydroxy-16α-methylpregnan-11,20-dione (27.1.39), after which a 17α- hydroxyl group is added. This is done by a reaction with acetic anhydride in the presence of p-toluenesulfonic acid, forming the 3-acetoxy-17-enolacetate 27.1.40, which is epoxidized by perbenzoic acid 27.1.41, and the product is hydrolyzed by an alkali to give an oxyketone 27.1.42. Addition of another hydroxyl group at C21 is accomplished by subsequent bromination of a methyl group with molecular bromine, replacing the bromine atom with iodine, and reacting iodide with potassium acetate, which forms the corresponding acetoxyketone 27.1.43. The hydroxyl group at C3 is oxidized to a carbonyl by chromium(VI) oxide in pyridine, giving the 3,11,20-triketone 27.1.44, which again undergoes bromination by molecular bromine, but at position C4. Dehydrogenation of this compound is accomplished using semicarbazide, which results in the formation of an unsaturated triketone 27.1.45. In order to avoid formation of semicarbazones at the keto-groups at C3 and C20, the final product is treated with pyruvic acid. Semicarbazones are then specially formed at the keto-groups of C3 and C20, and the keto-group at C11 that does not take part in semicarbazone formation is reduced to hydroxyl group using sodium borohydride. After removing the protective semicarbzone groups, 21-O-acetoxy-16β-methylhydrocortisone (27.1.46) is formed. This is reacted with potassium acetate and transformed to the epoxide 27.1.49. Reacting this with hydrofluoric acid results in an opening of the epoxide ring, during which the fluorohydrin 27.1.50 is formed. Finally, microbiological dehydrogenation of this compound at C1–C2 and simultaneous deacetylation gives dexamethasone (27.1.51).

Veterinary Drugs and Treatments

Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intralesionally. The above listing is certainly not complete. For specific dosages and indications refer to the Doses section. High dose dexamethasone use for shock or CNS trauma is controversial; recent studies have not demonstrated significant benefit and it actually may cause increased deleterious effects.

Drug interactions

Potentially hazardous interactions with other drugsAldesleukin: avoid concomitant use.Antibacterials: metabolism accelerated by rifamycins; metabolism possibly inhibited by erythromycin; concentration of isoniazid possibly reduced.Anticoagulants: efficacy of coumarins and phenindione may be altered.Antiepileptics: metabolism accelerated by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidoneAntifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism possibly inhibited by itraconazole and ketoconazole; caspofungin concentration possibly reduced (may need to increase dose).Antivirals: concentration of indinavir, lopinavir, saquinavir and telaprevir possibly reduced; avoid with rilpivirine; concentration possibly increased by ritonavir.Ciclosporin: rare reports of convulsions in patients on ciclosporin and high-dose corticosteroids.Cobicistat: concentration possibly increased by cobicistat.Cytotoxics: possibly decreases axitinib concentration, increase dose of axitinib.Diuretics: enhanced hypokalaemic effects of acetazolamide, loop diuretics and thiazide diuretics.Netupitant: concentration of dexamethasone increased - halve dexamethasone dose.Vaccines: high dose corticosteroids can impair immune response to vaccines; avoid concomitant use with live vaccines.

Metabolism

Corticosteroids are metabolised mainly in the liver but also in other tissues, and are excreted in the urine. The slower metabolism of the synthetic corticosteroids with their lower protein-binding affinity may account for their increased potency compared with the natural corticosteroids. Up to 65% of a dose of dexamethasone is excreted in urine within 24 hours.

Purification Methods

Dexamethasone has been recrystallised from Et2O or small volumes of EtOAc. Its solubility in H2O is 10 mg/100mL at 25o; and is freely soluble in Me2CO, EtOH and CHCl3. [Arth et al. J Am Chem Soc 80 3161 1958; for the -methyl isomer see Taub et al. J Am Chem Soc 82 4025 1960, see Beilstein 8 IV 3501.]

References

1) Merck Index 14 2943

Check Digit Verification of cas no

The CAS Registry Mumber 50-02-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 50-02:
(4*5)+(3*0)+(2*0)+(1*2)=22
22 % 10 = 2
So 50-02-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15?,16+,17+,19+,20+,21+,22+/m1/s1

50-02-2 Well-known Company Product Price

  • Brand
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  • CAS number
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  • Detail
  • Alfa Aesar

  • (A17590)  Dexamethasone, 98%   

  • 50-02-2

  • 1g

  • 881.0CNY

  • Detail
  • Alfa Aesar

  • (A17590)  Dexamethasone, 98%   

  • 50-02-2

  • 5g

  • 1811.0CNY

  • Detail
  • Alfa Aesar

  • (A17590)  Dexamethasone, 98%   

  • 50-02-2

  • 25g

  • 5377.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001593)  Dexamethasone for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 50-02-2

  • Y0001593

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001177)  Dexamethasone for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 50-02-2

  • Y0001177

  • 1,880.19CNY

  • Detail
  • Sigma

  • (D1756)  Dexamethasone  ≥98% (HPLC), powder

  • 50-02-2

  • D1756-25MG

  • 600.21CNY

  • Detail
  • Sigma

  • (D1756)  Dexamethasone  ≥98% (HPLC), powder

  • 50-02-2

  • D1756-100MG

  • 1,351.35CNY

  • Detail
  • Sigma

  • (D1756)  Dexamethasone  ≥98% (HPLC), powder

  • 50-02-2

  • D1756-500MG

  • 2,517.84CNY

  • Detail
  • Sigma

  • (D1756)  Dexamethasone  ≥98% (HPLC), powder

  • 50-02-2

  • D1756-1G

  • 3,958.11CNY

  • Detail
  • Sigma

  • (D1756)  Dexamethasone  ≥98% (HPLC), powder

  • 50-02-2

  • D1756-5G

  • 14,419.08CNY

  • Detail

50-02-2Synthetic route

C23H31FO4

C23H31FO4

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Stage #1: C23H31FO4 In ethyl acetate at 0 - 10℃;
Stage #2: With hydrogenchloride In water at 30 - 35℃; for 1h;
40%
betamethasone
1177-87-3

betamethasone

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;5%
With methanol; sodium carbonate at 20℃; for 0.166667h; Temperature;
16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one
1966-25-2

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; ethanol at 0℃; for 20h;
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
4: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one
14518-56-0

16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
2: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
3: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one
88509-22-2

9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
2: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 63 percent / sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
4: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
16α-methyl-17α,20;20,21-bismethylenedioxy-pregn-4,9(11)-diene-3-one
80163-63-9, 88509-13-1, 88548-10-1

16α-methyl-17α,20;20,21-bismethylenedioxy-pregn-4,9(11)-diene-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) LDA / 1.) THF, -78 deg C, 1 h then 0 deg C, 5 h; 2.) THF, -78 deg C, 3.5 h
2: 63 percent / sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
3: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
4: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
5: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl hydrogen (2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl)phosphoramidate

2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl hydrogen (2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl)phosphoramidate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
C24H35FNO8P

C24H35FNO8P

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 20 °C
2: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
C28H35FNO8P

C28H35FNO8P

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 20 °C
2: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
(9H-fluoren-9-yl)methyl (2-(((((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

(9H-fluoren-9-yl)methyl (2-(((((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: piperidine / dichloromethane / 3 h / 20 °C
2.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.67 h / 20 °C
2.2: 20 °C
3.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
C24H36FNO11P2

C24H36FNO11P2

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.67 h / 20 °C
1.2: 20 °C
2.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
(9H-fluoren-9-yl)methyl (4-(((((2-((8S,9R,10S,11S, 13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)phenyl)carbamate

(9H-fluoren-9-yl)methyl (4-(((((2-((8S,9R,10S,11S, 13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)phenyl)carbamate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: piperidine / dichloromethane / 20 °C
2.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.33 h / 20 °C
2.2: 20 °C
3.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
C28H36FNO11P2

C28H36FNO11P2

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.33 h / 20 °C
1.2: 20 °C
2.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
4-(2-(cyclooct-2-yn-1-yloxy)acetamido)phenyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

4-(2-(cyclooct-2-yn-1-yloxy)acetamido)phenyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
tert-butyl (2-(((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

tert-butyl (2-(((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethyl acetate / 1 h
2: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 20 °C
3: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
((9H-fluoren-9-yl)methyl) (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

((9H-fluoren-9-yl)methyl) (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) dihydrogen pyrophosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: piperidine / dichloromethane / 1.5 h / 20 °C
2.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
2.2: 20 °C
3.1: piperidine / dichloromethane / 1 h / 20 °C
4.1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
5.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogenpyrophosphate

(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogenpyrophosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 20 °C
2.1: piperidine / dichloromethane / 1 h / 20 °C
3.1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
4.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
(9H-fluoren-9-yl)methyl (2-(((((((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

(9H-fluoren-9-yl)methyl (2-(((((((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)ethyl)carbamate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: piperidine / dichloromethane / 1 h / 20 °C
2: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
3: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
2-amionethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogentriphosphate

2-amionethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogentriphosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C
2: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogen triphosphate

2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) trihydrogen triphosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) hydrogen phosphate

2-(2-(cyclooct-2-yn-1-yloxy)acetamido)ethyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) hydrogen phosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
tert-butyl (4-(((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)phenyl)carbamate

tert-butyl (4-(((2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)(hydroxy)phosphoryl)oxy)phenyl)carbamate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethyl acetate / 1 h
2: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 20 °C
3: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
4-(2-(cyclooct-2-yn-1-yloxy)acetamido)phenyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) hydrogen phosphate

4-(2-(cyclooct-2-yn-1-yloxy)acetamido)phenyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) hydrogen phosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
With rat liver lysosomes In water; dimethyl sulfoxide; acetonitrile at 37℃; for 6h; Enzymatic reaction;
dexamethasone phosphate
312-93-6, 360-63-4

dexamethasone phosphate

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / tert-butyl alcohol; water / 4 h / 100 °C
2: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 20 °C
2.1: piperidine / dichloromethane / 20 °C
3.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.33 h / 20 °C
3.2: 20 °C
4.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 20 °C
2.1: piperidine / dichloromethane / 3 h / 20 °C
3.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 0.67 h / 20 °C
3.2: 20 °C
4.1: rat liver lysosomes / water; acetonitrile; dimethyl sulfoxide / 6 h / 37 °C / Enzymatic reaction
View Scheme
dexamethasone
50-02-2

dexamethasone

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

dexamethasone 21-(p-nitrophenyl carbonate)
79360-11-5

dexamethasone 21-(p-nitrophenyl carbonate)

Conditions
ConditionsYield
With pyridine In chloroform Ambient temperature;100%
With pyridine In dichloromethane at 20℃; for 0.4h; Sealed tube;72%
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;55%
With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 4h;
With pyridine at 20℃; for 2h; Concentration;
dexamethasone
50-02-2

dexamethasone

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite
144490-31-3, 118362-03-1, 131349-31-0, 131349-37-6

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite

(2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)phosphite

(2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)phosphite

Conditions
ConditionsYield
Stage #1: dexamethasone; 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite With 5-(ethylthio)-1H-tetrazole In acetonitrile for 0.333333h;
Stage #2: With tert.-butylhydroperoxide In acetonitrile at 20℃; for 1h;
100%
dexamethasone
50-02-2

dexamethasone

terephthalic acid mono-tert-butyl ester
20576-82-3

terephthalic acid mono-tert-butyl ester

tert-butyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) terephthalate

tert-butyl (2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) terephthalate

Conditions
ConditionsYield
With pyridine; dmap; 1,2-dichloro-ethane at 20℃; for 18h; Inert atmosphere;100%
dexamethasone
50-02-2

dexamethasone

Fmoc-Asp-O-t-Bu
129460-09-9, 134098-70-7

Fmoc-Asp-O-t-Bu

1-(tert-butyl) 4-(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) (((9H-fluoren-9-yl)methoxy)carbonyl)-L-aspartate

1-(tert-butyl) 4-(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) (((9H-fluoren-9-yl)methoxy)carbonyl)-L-aspartate

Conditions
ConditionsYield
With pyridine; dmap; 1,2-dichloro-ethane In dichloromethane at 20℃; for 18h; Inert atmosphere;100%
dexamethasone
50-02-2

dexamethasone

9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid
37927-01-8

9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid

Conditions
ConditionsYield
Stage #1: dexamethasone With oxygen; potassium carbonate In methanol at 20℃; for 18h;
Stage #2: With hydrogenchloride In water
99%
With periodic acid In ethanol; water for 16.5h;97%
With sodium periodate; sulfuric acid In ethanol; water at 20℃; for 12h;97%
dexamethasone
50-02-2

dexamethasone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C28H43FO5Si

C28H43FO5Si

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 5h;98.5%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 4h;
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 4h;24.9 g
succinic acid anhydride
108-30-5

succinic acid anhydride

dexamethasone
50-02-2

dexamethasone

4-(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)-4-oxobutanoic acid

4-(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethoxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap In dichloromethane; acetonitrile at 20℃; for 2h;98%
With dmap In tetrahydrofuran for 48h; Darkness;94%
With pyridine; dmap at 20℃; Inert atmosphere;90%
dexamethasone
50-02-2

dexamethasone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Dexamethasone 21-mesylate
2265-22-7

Dexamethasone 21-mesylate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 3h; Inert atmosphere;96%
With pyridine at 4℃; for 16h; Inert atmosphere;83%
With pyridine for 17h; Inert atmosphere; Cooling with ice;83%
dexamethasone
50-02-2

dexamethasone

(12R)-hexanoyloxyoleic acid

(12R)-hexanoyloxyoleic acid

2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl (R,Z)-12-hexanoyloxyoleate

2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl (R,Z)-12-hexanoyloxyoleate

Conditions
ConditionsYield
Stage #1: (12R)-hexanoyloxyoleic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Cooling with ice; Inert atmosphere;
Stage #2: dexamethasone With dmap In dichloromethane for 17h; Cooling with ice; Inert atmosphere;
96%
dexamethasone
50-02-2

dexamethasone

disodium dexamethasone-21-phosphate

disodium dexamethasone-21-phosphate

Conditions
ConditionsYield
Stage #1: dexamethasone With pyrophosphoryl chloride In tetrahydrofuran at -50℃; for 1h;
Stage #2: With water In tetrahydrofuran at 20℃; pH=10;
Stage #3: With sodium hydroxide In toluene pH=10; Solvent;
95.9%
dexamethasone
50-02-2

dexamethasone

(R,Z)-4-((12-(hexanoyloxy)octadec-9-en-1-yl)oxy)-4-oxobutanoic acid

(R,Z)-4-((12-(hexanoyloxy)octadec-9-en-1-yl)oxy)-4-oxobutanoic acid

C50H77FO10

C50H77FO10

Conditions
ConditionsYield
Stage #1: (R,Z)-4-((12-(hexanoyloxy)octadec-9-en-1-yl)oxy)-4-oxobutanoic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Cooling with ice; Inert atmosphere;
Stage #2: dexamethasone With dmap In dichloromethane for 14h; Cooling with ice;
95%

50-02-2Relevant articles and documents

Antigen-Drug Conjugates as a Novel Therapeutic Class for the Treatment of Antigen-Specific Autoimmune Disorders

Pickens, Chad J.,Christopher, Matthew A.,Leon, Martin A.,Pressnall, Melissa M.,Johnson, Stephanie N.,Thati, Sharadvi,Sullivan, Bradley P.,Berkland, Cory

, p. 2452 - 2461 (2019)

Multiple sclerosis represents the world's most common cause of neurological disability in young people and is attributed to a loss of immune tolerance toward proteins of the myelin sheath. Typical treatment options for MS patients involve immunomodulatory drugs, which act nonspecifically, resulting in global immunosuppression. The study discussed herein aims to demonstrate the efficacy of antigen-specific immunotherapies involving the conjugation of disease causing autoantigen, PLP139-151, and a potent immunosuppressant, dexamethasone. Antigen-drug conjugates (AgDCs) were formed using copper-catalyzed azide-alkyne cycloaddition chemistry with the inclusion of a hydrolyzable linker to maintain the activity of released dexamethasone. Subcutaneous administration of this antigen-drug conjugates to SJL mice induced with experimental autoimmune encephalomyelitis, protected the mice from a symptom onset throughout the 25 day study, demonstrating enhanced efficacy in comparison to dexamethasone treatment. These results highlight the benefits of co-delivery of autoantigens with immunosuppressant drugs as AgDCs for the treatment of autoimmune diseases.

Synthesis method and application of 9-fluorosteroid compound

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Paragraph 0089-0096; 0134-0136, (2021/01/15)

The invention provides a synthesis method and application of a 9-fluorosteroid compound, and relates to the technical field of chemical synthesis. The synthesis method of the 9-fluorosteroid compoundcomprises the following step: reacting a compound II in an ionic liquid containing hydrogen fluoride salt to obtain a 9-fluorosteroid compound III. According to the synthesis method of the 9-fluorosteroid compound, the ionic liquid containing the hydrogen fluoride salt is used as a fluorinating agent to replace a traditional hydrogen fluoride aqueous solution, volatilization of hydrogen fluoride gas is avoided, corrosivity is small, toxicity is greatly reduced, reaction conditions are mild, reaction can be completed at the room temperature, operability is high, the safety coefficient is high,and production applicability is improved. The synthesis method of the 9-fluorosteroid compound is used for preparing corticosteroid drugs, highly toxic chemical reagents are not used in the synthesisroute, the operability is high, the safety coefficient is high, and the production applicability is improved.

Ring opening and fluoridation method and device of steroidal epoxy compound

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Paragraph 0038; 0039; 0041, (2017/07/22)

The invention discloses a method of preparing a compound II, which is as shown as the following reaction formula as shown in the specification. A 9 alpha-fluorine-11 beta -hydroxyl steroidal compound II is prepared via epoxy compound ring opening and fluoridation of a steroidal epoxy compound I by taking hydrogen fluoride as a fluorination reagent in a solvent consisting of arene and water. In the formula, R is CH3, CH2OH or CH2OAc; R1 is OH; R2 is alpha-CH3 or beta-CH3; and R3 is F or H. A continuous reaction device as shown in Figure 1 can be used in the method.

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