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24916-90-3

Basic Information
CAS No.: 24916-90-3
Name: 16-beta Methyl Epoxide
Article Data: 9
Molecular Structure:
Molecular Structure of 24916-90-3 (16-beta Methyl Epoxide)
Formula: C22H28O5
Molecular Weight: 372.461
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;
EINECS: 246-529-2
Density: 1.324 g/cm3
Melting Point: 210-220 °C
Boiling Point: 564.9 °C at 760 mmHg
Flash Point: 198.103 °C
Appearance: pale-yellow solid
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With dmap; methanesulfonyl chloride In dichloromethane for 4h; Heating;A 69%
B 1.1%
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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