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50-02-2 Usage

Chemical Properties

White or almost white, crystalline powder.

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 chemicalbook of Dai Xiongfeng.

Description

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.

Uses

Glucocorticoid.

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.

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-.

Chemical 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).

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.]

Therapeutic Function

9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione

Fire Hazard

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

Uses

Dexamethasone is used for the same indications as all corticosteroids; however, it exhibits a significantly more powerful anti-inflammatory and anti-allergic action. It is used for circulatory collapse—shock during or after surgical operations, trauma, blood loss, myocardial infarction, and burns. It is also used in severe infections—toxemia, vascular collapse in meningococcosis, septicemia, diphtheria, typhoid fever, and peritonitis. It is used in severe allergic conditions—asthmatic status, laryngeal edema, severe anaphylactic reactions to medicinal drugs, and pyrogenic reactions.

Air & Water Reactions

Insoluble in water.

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.

Description

Dexamethasone is an Anti-inflammatory glucocorticoid that is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is useful to study apoptosis, cell signaling pathways and gene expression. It is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine to treat difficult ear infections in dogs. It is also used to treat horses with swelling of of distal limbs and general bruising in combination with trichlormethiazide. Dexamethasone induces the production of phospholipase A2 inhibitory protein (lipocortin). It also inhibits induction of nitric oxide synthase (IC50=5 nM). Dexamethasone has been shown to cause reduction in cyclin A and Cd k2 activity, inhibition of G1/S transition in osteoblasts and inhibition of phosphorylation of Rb protein in vitro. Dexamethasone has been observed to induce apoptosis in human thymocytes and eosinophils, but inhibits apoptosis in neutrophils in vitro. Dexamethasone is an activator of IDO. Dexamethasone Inhibits the expression of the inducible but not the constitutive nitric oxide synthase in vascular endothelial cells (IC50=5 nM). Dexamethasone regulates T cell survival, growth, and differentiation.Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+-K+ pump. Has anti-inflammatory and anti-rheumatic properties. Induces apoptosis in human thymocytes. In general, 500-1000 nM of dexamethasone is sufficient to induce apoptosis following a 6-hour incubation at 37°C.

Brand name

Aeroseb-Dex (Allergan); Decadron (Merck); Dexone (Solvay Pharmaceuticals); Hexadrol (Organon); Maxidex (Alcon); Mymethasone (Morton Grove).

Biological Activity

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

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.

Manufacturing Process

The preparation of dexamethasone acetate is described in US Patent 3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydrous hydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (prepared according to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). The steroid dissolves in about 15 minutes. The reaction mixture is shaken for two hours at a temperature between 0 and +5°C, and then poured into 75 cc ofwater containing in suspension, 7.5 grams of sodium bicarbonate. The mixture is vacuum filtered, the filter cake washed and then dried at 100°C, yielding 460 mg of crude hexadecadrol contaminated with a small amount of the starting material. A single recrystallization from methylene chloride yields 370 mg of the pure product having a melting point of 170°C and 229°C. The mother liquor yields 62 mg of the starting material, and a remainder constituting a mixture of starting and final materials with little other contamination.

Originator

Dexacen,Central,US,1977

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.

General Description

Odorless white to off-white crystalline powder with a slightly bitter taste.

General Description

Dexamethasone, 9-fluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione,is the 16 -isomer of betamethasone.Dexamethasone acetate, USP (21-acetate)Dexamethasone sodium phosphate, USP (21-sodiumphosphate).

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
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 (Code)Product description CAS number Packaging Price 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%

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