3275-64-7

Basic information

• Product Name: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
• Synonyms: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;Nsc63329;Madol;(5alpha,17beta)-17-Methylandrost-2-en-17-ol;17a-methyl-etioallocholan-2-ene;Androst-2-en-17-ol,17-methyl-, (5a,17b)-;(5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenthren-17-ol;17-Methyl-5-alpha-androst-2-en-17-beta-ol
• CAS NO: 3275-64-7
• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.46748
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 3275-64-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 144-146?C
• Boiling Point: 370.69°C (rough estimate)
• Flash Point: 160.866 °C
• Appearance: /
• Density: 0.9789 (rough estimate)
• Vapor Pressure: 2.72E-07mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Refrigerator
• PKA: 15.16±0.60(Predicted)
• CAS DataBase Reference: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(3275-64-7)
• EPA Substance Registry System: (5S,8S,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol(3275-64-7)

Safety Data

• Hazardous Substances Data: 3275-64-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

It is an anabolic er as compared to dihydrotestosterone (DHT).

InChI:InChI=1/C20H32O/c1-18-11-5-4-6-14(18)7-8-15-16(18)9-12-19(2)17(15)10-13-20(19,3)21/h4-5,14-17,21H,6-13H2,1-3H3/t14-,15-,16+,17+,18+,19+,20+/m1/s1

Synthetic route

5α-androst-2-en-17-one (14639-79-3, 24174-20-7, 82467-84-3, 963-75-7) + methylmagnesium bromide (75-16-1) → 17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	39%
In diethyl ether; benzene

2α-bromo-17β-hydroxy-5α-androstan-3-one (29041-91-6) → 17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NaBH4, EtOH, (ii) Zn, AcOH, (iii) NaOH, MeOH 2: CrO3, H2SO4 / acetone 3: diethyl ether; benzene View Scheme

(5α,17β)-androst-2-en-17-ol (2639-53-4) → 17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3, H2SO4 / acetone 2: diethyl ether; benzene View Scheme

Epiandrosterone (481-29-8) → 17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) + 17β-hydroxy-17α-methyl-5α-androstan-3-ene (62797-46-0, 94901-78-7, 1229-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: 2,6-dimethylpyridine / Heating View Scheme

3β-tosyloxy-5α-androstan-17-one (10429-07-9) + methylmagnesium bromide (75-16-1) → 17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) + 17β-hydroxy-17α-methyl-5α-androstan-3-ene (62797-46-0, 94901-78-7, 1229-05-6)

Conditions	Yield
Stage #1: 3β-tosyloxy-5α-androstan-17-one With 2,6-dimethylpyridine Heating; Stage #2: methylmagnesium bromide In tetrahydrofuran

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 2,3-epoxy-17-methyl-androstan-17-ol (968-54-7)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 5h; Ambient temperature;	95%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h; Inert atmosphere;	91%

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 17-methyl-5α-androstane-3α,17β-diol (641-82-7)

Conditions	Yield
(i) B2H6, THF, (ii) aq. H2O2, NaOH; Multistep reaction;
(i) B2H6, (ii) aq. H2O2, OH-; Multistep reaction;

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 2α,17β-Dihydroxy-17α-methyl-androstan (98243-02-8)

Conditions	Yield
(i) B2H6, THF, (ii) aq. H2O2, NaOH; Multistep reaction;
(i) B2H6, (ii) aq. H2O2, OH-; Multistep reaction;

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → (2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carbonitrile (141691-37-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature 2: 98 percent / toluene / 4 h / Ambient temperature View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → C21H33(2)HO4 (141691-39-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature 2: 98 percent / toluene / 4 h / Ambient temperature 3: 10.6 percent / D2O, CH3OD, Ba(OH)2 / 48 h / 80 °C View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → (2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carboxylic acid (141691-38-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / m-chloroperoxybenzoic acid / CHCl3 / 5 h / Ambient temperature 2: 98 percent / toluene / 4 h / Ambient temperature 3: 13 percent / aq. Ba(OH)2 / acetone / 48 h / 80 °C View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → mestanolone (521-11-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) B2H6, THF, (ii) aq. H2O2, NaOH 2: CrO3, aq. H2SO4 / acetone View Scheme
Multi-step reaction with 2 steps 1: (i) B2H6, (ii) aq. H2O2, OH- 2: aq. CrO3 View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 17α-Methyl-2-methylen-androstanol-(17β)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) B2H6, THF, (ii) aq. H2O2, NaOH 2: CrO3, aq. H2SO4 / acetone; dioxane 3: (i) nBuLi, Et2O, (ii) /BRN= 7193671/, THF View Scheme
Multi-step reaction with 3 steps 1: (i) B2H6, (ii) aq. H2O2, OH- 2: aq. CrO3 View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 17α-Methyl-5α-androstan-17β-ol-2-on (10455-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) B2H6, THF, (ii) aq. H2O2, NaOH 2: CrO3, aq. H2SO4 / acetone; dioxane View Scheme
Multi-step reaction with 2 steps 1: (i) B2H6, (ii) aq. H2O2, OH- 2: aq. CrO3 View Scheme

17β-hydroxy-17α-methyl-5α-androst-2-ene (3275-64-7) → 17β-benzyloxy-17α-methyl-5α-androst-2-ene

Upstream product

• 14639-79-3 5α-androst-2-en-17-one 
• 75-16-1 methylmagnesium bromide 
• 29041-91-6 2α-bromo-17β-hydroxy-5α-androstan-3-one 
• 2639-53-4 (5α,17β)-androst-2-en-17-ol 
• 481-29-8 Epiandrosterone 
• 10429-07-9 3β-tosyloxy-5α-androstan-17-one 

Downstream Products

• 521-11-9 mestanolone 

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