(9b,11b,16a)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione supplier

Name
16-beta Methyl Epoxide
EINECS 246-529-2
CAS No. 24916-90-3
Article Data9
CAS DataBase
Density 1.324 g/cm³
Solubility
Melting Point 210-220 °C
Formula C₂₂H₂₈O₅
Boiling Point 564.9 °C at 760 mmHg
Molecular Weight 372.461
Flash Point 198.103 °C
Transport Information
Appearance pale-yellow solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 16α-Methyl Epoxide(8-DM);9b-Pregna-1,4-diene-3,20-dione,9,11b-epoxy-17,21-dihydroxy-16a-methyl- (7CI,8CI);Dexamethasone9,11-epoxide;(9β,11β,16α)-17,21-Dihydroxy-16-methyl-9,11-epoxypregna-1,4-dien-3,20-dion;AC1L3LOM;AC1Q5HK8;CID91242;AR-1C1025;
PSA 87.13000
LogP 1.96410

Synthetic route

: C26H33BrO8

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at 0 - 5℃;	93.3%

: 2884-51-7
17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With sodium hydroxide In methanol at -10 - -5℃; for 2h; Reagent/catalyst; Temperature;	84%
With water; sodium hydroxide In methanol; dichloromethane at -5 - 0℃; for 3h;

: 78761-59-8
11α,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / -15 °C 2: phosphorus pentachloride / tetrahydrofuran / -85 °C 3: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 4: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme

: Carbonic acid 2-((8S,9S,10R,11R,13S,14S,16R,17R)-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-oxo-ethyl ester ethyl ester

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus pentachloride / tetrahydrofuran / -85 °C 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 3: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme

: 89561-92-2
17α-hydroxy-16α-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C 2: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 159264-49-0
9,11-epoxy-17α-hydroxy-16α-methyl-3-oxandrosta-1,4-diene-17β-carboxylic acid

Conditions

Conditions	Yield
With periodic acid In tetrahydrofuran; water at 0 - 5℃; for 2h;	98.7%

: 108-24-7
acetic anhydride

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 2884-51-7
17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate

Conditions

Conditions	Yield
With potassium acetate In ISOPROPYLAMIDE at 20℃; for 2h;	98%

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 83881-08-7
21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With Vilsmeier reagent In tetrahydrofuran Reagent/catalyst; Solvent; Inert atmosphere;	86%
Multi-step reaction with 2 steps 1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 5 °C 2: CH2Cl2; methanol / 3.5 h / 40 - 42 °C View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 124-63-0
methanesulfonyl chloride

: 223776-47-4
17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-methanesulfonate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 4h; Ambient temperature;	84%
With pyridine at -5 - 0℃; for 5h;

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

A: 83881-08-7
21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

B: 223776-51-0
9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one

Conditions

Conditions	Yield
With dmap; methanesulfonyl chloride In dichloromethane for 4h; Heating;	A 69% B 1.1%

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 124-63-0
methanesulfonyl chloride

A: 83881-08-7
21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

B: 223776-51-0
9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one

Conditions

Conditions	Yield
With dmap In dichloromethane for 4h; Heating;	A 69% B 1.1%

...Expand

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 134429-25-7
C22H28O6

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 1h;	33.5%

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 98-59-9
p-toluenesulfonyl chloride

: 9β,11β-epoxy-17α,21-dihydroxy-16α-methyl-1,4-pregnadien-3,20-dione 21-tosylate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 5℃;
With triethylamine hydrochloride In dichloromethane at -5 - 5℃; for 9h;

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 105102-22-5
mometasone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / 4-DMAP, CH3SO2Cl / CH2Cl2 / 4 h / Heating 2: 83 percent / conc. HCl / acetic acid / 3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 69 percent / 4-DMAP / CH2Cl2 / 4 h / Heating 2: 83 percent / conc. HCl / acetic acid / 3 h / Ambient temperature View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 83919-23-7
Mometasone furoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / 4-DMAP, CH3SO2Cl / CH2Cl2 / 4 h / Heating 2: 3.44 g / Et3N, 4-DMAP / CH2Cl2 / 6 h / Ambient temperature 3: 83 percent / conc. HCl / acetic acid / 3 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 69 percent / 4-DMAP / CH2Cl2 / 4 h / Heating 2: 3.44 g / Et3N, 4-DMAP / CH2Cl2 / 6 h / Ambient temperature 3: 83 percent / conc. HCl / acetic acid / 3 h / Ambient temperature View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 83881-09-8
9,11-Epoxidemometasone furoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / 4-DMAP, CH3SO2Cl / CH2Cl2 / 4 h / Heating 2: 3.44 g / Et3N, 4-DMAP / CH2Cl2 / 6 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 69 percent / 4-DMAP / CH2Cl2 / 4 h / Heating 2: 3.44 g / Et3N, 4-DMAP / CH2Cl2 / 6 h / Ambient temperature View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 9β,11β-epoxy-16α-methyl-17α,21-oxidopregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / Et3N / tetrahydrofuran / 4 h / Ambient temperature 2: 80 percent / DBU / CH2Cl2 / 2 h / Heating View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 223776-50-9
17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.1 percent / 4-DMAP, CH3SO2Cl / CH2Cl2 / 4 h / Heating 2: 10 mg / 4-DMAP, Et3N / CH2Cl2 / 5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 1.1 percent / 4-DMAP / CH2Cl2 / 4 h / Heating 2: 10 mg / 4-DMAP, Et3N / CH2Cl2 / 5 h / Ambient temperature View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 9α-chloro-11β,17α-dihydroxy-17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.1 percent / 4-DMAP, CH3SO2Cl / CH2Cl2 / 4 h / Heating 2: 10 mg / 4-DMAP, Et3N / CH2Cl2 / 5 h / Ambient temperature 3: 87 percent / conc. HCl / acetic acid / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1.1 percent / 4-DMAP / CH2Cl2 / 4 h / Heating 2: 10 mg / 4-DMAP, Et3N / CH2Cl2 / 5 h / Ambient temperature 3: 87 percent / conc. HCl / acetic acid / 2 h / Ambient temperature View Scheme

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-(4-dimethylaminopyridinium methanesulfonate)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / Et3N / tetrahydrofuran / 4 h / Ambient temperature 2: 91 percent / CH2Cl2 / 3 h / Heating View Scheme

: 69739-34-0
t-butyldimethylsiyl triflate

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 9β,11β-epoxy-3,21-di(t-butyldimethylsilyloxy)-17α-hydroxy-16α-methylpregna-1,3,5-triene-20-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -4 - 20℃; for 0.25h;

: 75-09-2
dichloromethane

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 98-59-9
p-toluenesulfonyl chloride

: 83881-08-7
21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With triethylamine In methanol; water

...Expand

: methanol-dichloromethane

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 23961-95-7
epoxyparamethasone

Conditions

Conditions	Yield
methanolic potassium hydroxide

: 24916-90-3
17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

: 98-59-9
p-toluenesulfonyl chloride

: 83881-08-7
21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With triethylamine In methanol; dichloromethane; water

(9b,11b,16a)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione Specification

The 9beta,11beta-Epoxy-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione with CAS registry number of 24916-90-3 is also known as (9b,11b,16a)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione. The systematic name is (9β,11β,16α)-17,21-dihydroxy-16-methyl-9,11-epoxypregna-1,4-diene-3,20-dione. It belongs to product categories of Pharmaceutical Raw Materials; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. Its EINECS registry number is 246-529-2. In addition, the formula is C₂₂H₂₈O₅ and the molecular weight is 372.45. This chemical is a pale-yellow solid and should be stored in sealed containers in dry and ventilated place and away from oxidizing agents and light. Besides, this chemical is used as intermediate of betamethasone.

Physical properties about 9beta,11beta-Epoxy-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione are: (1)ACD/LogP: 0.97; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 29; (6)ACD/BCF (pH 7.4): 29; (7)ACD/KOC (pH 5.5): 389; (8)ACD/KOC (pH 7.4): 389; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.616; (13)Molar Refractivity: 98.283 cm³; (14)Molar Volume: 281.203 cm³; (15)Surface Tension: 58.309 dyne/cm; (16)Density: 1.324 g/cm³; (17)Flash Point: 198.103 °C; (18)Enthalpy of Vaporization: 97.498 kJ/mol; (19)Boiling Point: 564.935 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 9beta,11beta-Epoxy-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione: it can be prepared by hecogenin through acetylation, elimination (dehydrogenation), reduction, open-loop, epoxidation, acetylation, ketal reaction, addition, bromination, substitution, oxidation, elimination, addition, cyclization and so on.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C35C(O5)CC2(C1(C(=O)CO)O)C)C
2. InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)22(15)18(27-22)10-20(16,3)21(12,26)17(25)11-23/h6-7,9,12,15-16,18,23,
26H,4-5,8,10-11H2,1-3H3
3. InChIKey: GBDXNHBVYAMODG-UHFFFAOYSA-N

Product Name

16-beta Methyl Epoxide

Synthetic route

(9b,11b,16a)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione Specification

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