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50-02-2 Usage

Brand name

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

Fire Hazard

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

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.

General Description

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

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.

Biological Activity

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

Uses

Glucocorticoid.

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.

Air & Water Reactions

Insoluble in water.

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.]

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
Sigma (D1756)  Dexamethasone  ≥98% (HPLC), powder 50-02-2 D1756-5G 14,419.08CNY 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 D1756-500MG 2,517.84CNY 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 D1756-25MG 600.21CNY Detail
Sigma-Aldrich (Y0001177)  Dexamethasone for system suitability  European Pharmacopoeia (EP) Reference Standard 50-02-2 Y0001177 1,880.19CNY Detail
Sigma-Aldrich (Y0001593)  Dexamethasone for peak identification  European Pharmacopoeia (EP) Reference Standard 50-02-2 Y0001593 1,880.19CNY Detail
Alfa Aesar (A17590)  Dexamethasone, 98%    50-02-2 25g 5377.0CNY Detail
Alfa Aesar (A17590)  Dexamethasone, 98%    50-02-2 5g 1811.0CNY Detail
Alfa Aesar (A17590)  Dexamethasone, 98%    50-02-2 1g 881.0CNY 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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