Dexamethasone supplier | CasNO.50-02-2

Name
Dexamethasone
EINECS 200-003-9
CAS No. 50-02-2
Article Data39
CAS DataBase
Density 1.32 g/cm³
Solubility 10 mg/100 mL (25 °C) in water
Melting Point 262-264 °C(lit.)
Formula C₂₂H₂₉FO₅
Boiling Point 568.2 °C at 760 mmHg
Molecular Weight 392.468
Flash Point 297.5 °C
Transport Information
Appearance White crystalline solid
Safety 36/37-45-36-26-22
Risk Codes 43-40-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Diodex;Etacortilen;Fluormone;Fluorocort;Gammacorten;HL-Dex;Hexadecadrol;Hexadrol;Isopto-Dex;Loverine;Luxazone;Millicorten;Oradexon;Pet-Derm III;Prednisolone F;Superprednol;Surodex;Visumetazone;Pregna-1,4-diene-3,20-dione,9-fluoro-11,17,21-trihydroxy-16-methyl-, (11b,16a)-;Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16a-methyl- (6CI,8CI);1-Dehydro-16a-methyl-9a-fluorohydrocortisone;16a-Methyl-9a-fluoro-D1-hydrocortisone;16a-Methyl-9a-fluoroprednisolone;9-Fluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione;9a-Fluoro-16a-methyl-1,4-pregnadiene-11b,17a,21-triol-3,20-dione;9a-Fluoro-16a-methyl-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione;9a-Fluoro-16a-methylprednisolone;Adexone;Aeroseb-Dex;Aphtasolon;Aphthasolone;Azium;Calonat;Corsone;Decacort;Decaderm;Decadron;Decadron A;Dekort;Delipos;Dergramin;Desameton;Dexa-Cortidelt;Dexa-Scheroson;Dexacortin;Dexalona;Dexamethasone alcohol;Dexapolcort;Dexaprol;Dexason;Dexinoral;Dexmethsone;Dexonium;Dinormon;
PSA 94.83000
LogP 1.89570

Synthetic route

: C23H31FO4

: 50-02-2
dexamethasone

Conditions

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

: 1177-87-3
betamethasone

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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;

: 1966-25-2
16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
With hydrogen fluoride In tetrahydrofuran; ethanol at 0℃; for 20h;

: 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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 14518-56-0
16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 88509-22-2
9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 88509-18-6, 88509-19-7
C30H36O5Se

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 80163-63-9, 88509-13-1, 88548-10-1
16α-methyl-17α,20;20,21-bismethylenedioxy-pregn-4,9(11)-diene-3-one

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

Yield

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

: 50-02-2
dexamethasone

Conditions

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

: C24H35FNO8P

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

Yield

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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

Conditions

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

: 312-93-6, 360-63-4
dexamethasone phosphate

: 50-02-2
dexamethasone

Conditions

Conditions	Yield
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

: 50-02-2
dexamethasone

: 7693-46-1
4-Nitrophenyl chloroformate

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

Conditions

Conditions	Yield
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;

: 50-02-2
dexamethasone

: 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

Conditions

Conditions	Yield
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%

: 50-02-2
dexamethasone

: 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

Conditions

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

: 50-02-2
dexamethasone

: 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

Conditions

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

: 50-02-2
dexamethasone

: 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

Conditions	Yield
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%

: 50-02-2
dexamethasone

: 18162-48-6
tert-butyldimethylsilyl chloride

: C28H43FO5Si

Conditions

Conditions	Yield
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

: 108-30-5
succinic acid anhydride

: 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

Conditions

Conditions	Yield
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%

: 50-02-2
dexamethasone

: 124-63-0
methanesulfonyl chloride

: 2265-22-7
Dexamethasone 21-mesylate

Conditions

Conditions	Yield
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%

: 50-02-2
dexamethasone

: (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

Conditions

Conditions	Yield
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%

: 50-02-2
dexamethasone

: disodium dexamethasone-21-phosphate

Conditions

Conditions	Yield
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%

: 50-02-2
dexamethasone

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

: C50H77FO10

Conditions

Conditions	Yield
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%

Dexamethasone Specification

1. Introduction of Dexamethasone
Dexamethasone is a synthetic corticosteroid with approximately 25 times the anti-inflammatory potency of naturally occurring cortisol. The IUPAC Name of it is (8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one. Dexamethasone commonly is used in both small- and large-animal veterinary medicine. It may be given by injection, inhalation orally or topically. Preparations for topical use may include other active ingredients such as antibiotics, antifungals or miticides.

2. Properties of Dexamethasone
Index of Refraction: 1.591
Molar Refractivity: 100.23 cm³
Molar Volume: 296.2 cm³
Surface Tension: 56.5 dyne/cm
Density: 1.32 g/cm³
Flash Point: 297.5 °C
Enthalpy of Vaporization: 97.96 kJ/mol
Boiling Point: 568.2 °C at 760 mmHg
Vapour Pressure: 2.81E-15 mmHg at 25 °C
Melting point: 262-264 °C(lit.)
Storage tempreture: 2-8 °C
Solubility: Ethanol: 1 mg/mL
Appearance: White crystalline solid

3. Toxicity of Dexamethasone

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	410mg/kg (410mg/kg)		Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 281, 1970.
mouse	LD50	subcutaneous	4400mg/kg (4400mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2117, 1979.
rabbit	LD50	subcutaneous	7200ug/kg (7.2mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat	LD50	intraperitoneal	54mg/kg (54mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat	LD50	oral	> 3gm/kg (3000mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 28, Pg. 687, 1984.
rat	LD50	subcutaneous	14mg/kg (14mg/kg)		Toxicology and Applied Pharmacology. Vol. 8, Pg. 250, 1966.
women	TDLo	multiple routes	4759ug/kg/18D (4.759mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	Intensive Care Medicine. Vol. 21, Pg. 238, 1995.

4. Safety Information of Dexamethasone

Hazard Codes: Irritant Xi, Harmful Xn
Risk Statements: 43-40-36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R40:Limited evidence of a carcinogenic effect.
R43:May cause sensitization by skin contact.
Safety Statements: 36/37-45-36-26-22
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

5. Preparation of Dexamethasone
Dexamethasone is reacted with a source of hypobromite, such as basic N-bromosuccinimide, to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with hydrogen fluoride in tetrahydrofuran gives dexamethasone.

6. Use of Dexamethasone
Dexamethasone is used to treat many inflammatory and autoimmune conditions. If given in high doses, it is useful to counteract allergic anaphylactic shock. It is used in transvenous screw-in cardiac pacing leads to minimize the inflammatory response of the myocardium. In oncology, it is given to cancer patients undergoing chemotherapy to counteract certain side-effects of their antitumor treatment. It is also used in the treatment of high altitude cerebral edema as well as pulmonary edema. Dexamethasone is also used in a diagnostic context namely in its property to suppress the natural pituitary-adrenal axis.

7. Side effect of Dexamethasone
Dexamethasone may have such sife effects:
1)Stomach upset, increased sensitivity to stomach acid to the point of ulceration of esophagus, stomach, and duodenum.
2)Increased appetite leading to significant weight gain
3)A latent diabetes mellitus often becomes manifest, glucose intolerance is worsened in patients with pre-existing diabetes
4)Immunsuppressant action, particularly if given with other immunosuppressants, such as cyclosporine, may allow bacterial, viral, and fungal disease to progress more easily and can become life-threatening; fever as a warning symptom is often suppressed.
5)Psychiatric disturbances, including personality changes, irritability, euphoria, or mania and mood swings.

8. Other details of Dexamethasone
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones, and acts as an anti-inflammatory and immunosuppressant. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.

Product Name

Dexamethasone

Synthetic route

Dexamethasone Specification

Related Products

Hot Products