5alpha-Androst-16-en-3beta-ol supplier

Name
16,(5-ALPHA)-ANDROSTEN-3-BETA-OL
EINECS 214-573-1
CAS No. 7148-51-8
Article Data27
CAS DataBase
Density 1.037 g/cm³
Solubility
Melting Point 123-124 °C
Formula C₁₉H₃₀O
Boiling Point 374.1 °C at 760 mmHg
Molecular Weight 274.447
Flash Point 156.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5a-Androst-16-en-3b-ol (6CI,7CI,8CI);3b-Hydroxy-5a-androst-16-ene;JNF 55;NSC65888;
PSA 20.23000
LogP 4.55610

Synthetic route

: 18339-16-7
5α-androst-16-en-3-one

A: 7148-51-8
5α-androst-16-en-3β-ol

B: 3597-54-4, 4572-71-8, 7148-51-8, 14152-27-3, 18485-74-0, 19321-55-2, 64681-01-2, 86335-09-3, 86335-14-0, 86335-15-1, 103615-88-9, 103615-90-3, 1153-51-1
androstenol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol for 2h; Ambient temperature;	A 77% B 2%
With aluminum isopropoxide; isopropyl alcohol Isolierung ueber die in wss. Aethanol schwer loesliche Verbindung mit Digitonin;
With ethanol; water; lithium tri-sec-butyl(hydrido)borate 1.) THF, r.t., 3 h; 2.) -55 deg C; Yield given. Multistep reaction. Yields of byproduct given;

: 95043-81-5
17-iodo-3β-hydroxy-5α-androstan-16-ene

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With diethylene glycol monoethyl ether sodium salt In 1,4-dioxane at 100℃; for 92h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	75.4%
With ethanol; sodium Heating;
With sodium In ethanol Reflux;

: 939496-37-4
16R-bromopregnane-3S,20S-diol

A: 16S,20S-epoxypregnane-3S-ol

B: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 60℃; for 18h;	A 65% B 30%
With potassium tert-butylate In tert-butyl alcohol at 82℃; for 5h;	A 46% B 52%

: 481-29-8
Epiandrosterone

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Stage #1: Epiandrosterone With toluene-4-sulfonic acid hydrazide In ethanol for 2h; Bamford-Stevens Decomposition; Reflux; Stage #2: With methyllithium In diethyl ether at 22℃; for 16.5h; Bamford-Stevens Decomposition;	29%

: 18339-16-7
5α-androst-16-en-3-one

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

: 18339-16-7
5α-androst-16-en-3-one

: 555-31-7
aluminum isopropoxide

: 67-63-0
isopropyl alcohol

A: 7148-51-8
5α-androst-16-en-3β-ol

B: 3597-54-4, 4572-71-8, 7148-51-8, 14152-27-3, 18485-74-0, 19321-55-2, 64681-01-2, 86335-09-3, 86335-14-0, 86335-15-1, 103615-88-9, 103615-90-3, 1153-51-1
androstenol

...Expand

: 72203-76-0
5α-androst-16-en-3β-yl acetate

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With potassium hydroxide In methanol

: 94438-53-6
17-bromo-3β-hydroxy-5α-androstan-16-ene

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With ethanol; sodium Heating;

: 17320-46-6
17-chloro-3β-hydroxy-5α-androstan-16-ene

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
With sodium amide In diethyl ether
With ethanol; sodium
With ethanol; sodium Heating;

: 521-18-6
Stanolone

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / pyridine / 24 h / 0 °C 2: 87 percent / toluene / 480 °C 3: 1.) lithium tris(1,2-dimethylpropyl)hydridoborate; 2.) water, ethanol / 1.) THF, r.t., 3 h; 2.) -55 deg C View Scheme

: 19291-29-3
17β-methoxycarbonyloxy-5α-androstan-3-one

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / toluene / 480 °C 2: 1.) lithium tris(1,2-dimethylpropyl)hydridoborate; 2.) water, ethanol / 1.) THF, r.t., 3 h; 2.) -55 deg C View Scheme

: 1239-31-2
3β-acetoxy-5α-androstan-17-one

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 2.4 g / hydroxylamine hydrochloride / pyridine / 3 h / 60 °C 2: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 4: 0.41 g / pyridine / 12 h / Ambient temperature 5: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 5 steps 1: 2.4 g / hydroxylamine hydrochloride / pyridine / 3 h / 60 °C 2: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 4: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 5: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 5 steps 1: 2.4 g / hydroxylamine hydrochloride / pyridine / 3 h / 60 °C 2: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 3: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 4: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 5: 2percent potassium hydroxide / methanol View Scheme

: 86270-19-1
17-nitroimino-5α-androstan-3β-yl acetate

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 2: 0.41 g / pyridine / 12 h / Ambient temperature 3: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 3 steps 1: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 2: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 3: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 3 steps 1: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 2: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 3: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 3 steps 1: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 2: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 3: 2percent potassium hydroxide / methanol View Scheme

: 86270-21-5
17β-nitroamino-5α-androstan-3β-yl acetate

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.41 g / pyridine / 12 h / Ambient temperature 2: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 2 steps 1: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 2: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 2 steps 1: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 2: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 2 steps 1: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 2: 2percent potassium hydroxide / methanol View Scheme

: 23498-55-7
(3β,5α)-3-(acetyloxy)androstan-17-one 17-oxime

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 3: 0.41 g / pyridine / 12 h / Ambient temperature 4: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 4 steps 1: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 3: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 4: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 4 steps 1: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 3: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 4: 2percent potassium hydroxide / methanol View Scheme
Multi-step reaction with 4 steps 1: 0.68 g / sodium nitrite, acetic acid / CH2Cl2 / 1 h / Ambient temperature 2: 75 percent / sodium borohydride / ethanol / 1.5 h / Ambient temperature 3: 0.41 g / pyridine, acetic anhydride / 12 h / Ambient temperature 4: 2percent potassium hydroxide / methanol View Scheme

: 10481-80-8
3β-hydroxy-17-hydrozone-5α-androstane

: 7148-51-8
5α-androst-16-en-3β-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-chloro-succinimide, Py 2: Na, EtOH View Scheme
Multi-step reaction with 2 steps 1: NBS, Py 2: Na, EtOH / Heating View Scheme
Multi-step reaction with 2 steps 1: I2, Et3N 2: Na, EtOH / Heating View Scheme
Multi-step reaction with 2 steps 1: N-chloro-succinimide, Py 2: Na, EtOH / Heating View Scheme

: 591-17-3
meta-bromotoluene

: 94438-53-6
17-bromo-3β-hydroxy-5α-androstan-16-ene

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(3’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
Stage #1: 17-bromo-3β-hydroxy-5α-androstan-16-ene With tert.-butyl lithium; XPhos In tetrahydrofuran; pentane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: meta-bromotoluene With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; toluene; pentane at -78 - 20℃; Temperature;	A n/a B 44 %Spectr.

...Expand

: 95-46-5
2-methylphenyl bromide

: 94438-53-6
17-bromo-3β-hydroxy-5α-androstan-16-ene

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(2’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
Stage #1: 17-bromo-3β-hydroxy-5α-androstan-16-ene With tert.-butyl lithium; XPhos In tetrahydrofuran; pentane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 2-methylphenyl bromide With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; toluene; pentane at -78 - 20℃;	A n/a B 31 %Spectr.

...Expand

: 17878-44-3
(4-bromophenoxy)trimethylsilane

: 94438-53-6
17-bromo-3β-hydroxy-5α-androstan-16-ene

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(((4'-trimethylsilyl)ethynyl)phenyl)androst-16-en-3-ol

Conditions

Conditions	Yield
Stage #1: 17-bromo-3β-hydroxy-5α-androstan-16-ene With tert.-butyl lithium; XPhos In tetrahydrofuran; pentane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (4-bromophenoxy)trimethylsilane With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; toluene; pentane at -78 - 20℃;

...Expand

: 481-29-8
Epiandrosterone

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(2’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate; triethylamine / ethanol / 16 h / 50 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C 2.1: XPhos; tert.-butyl lithium / pentane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: hydrazine hydrate; triethylamine / ethanol / 16 h / 50 °C / Inert atmosphere 2: triethylamine; iodine / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / benzene; methanol; water / 24 h / Schlenk technique; Reflux View Scheme

: 481-29-8
Epiandrosterone

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(3’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate; triethylamine / ethanol / 16 h / 50 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C 2.1: XPhos; tert.-butyl lithium / pentane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: -78 - 20 °C View Scheme

: 481-29-8
Epiandrosterone

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(((4'-trimethylsilyl)ethynyl)phenyl)androst-16-en-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate; triethylamine / ethanol / 16 h / 50 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C 2.1: XPhos; tert.-butyl lithium / pentane; tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: -78 - 20 °C View Scheme

: 16419-60-6
2-Methylphenylboronic acid

: 95043-81-5
17-iodo-3β-hydroxy-5α-androstan-16-ene

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(2’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; benzene for 24h; Suzuki Coupling; Schlenk technique; Reflux; Overall yield = 22 mg;	A n/a B 31 %Spectr.

...Expand

: 10481-80-8
3β-hydroxy-17-hydrozone-5α-androstane

A: 7148-51-8
5α-androst-16-en-3β-ol

B: (3β,5α)-17-(2’-methylphenyl)-androst-16-en-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; iodine / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / benzene; methanol; water / 24 h / Schlenk technique; Reflux View Scheme

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 143101-95-5
3β-hydroxy-5α-androstane-16α-carboxylic acid methyl ester

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride at 100 - 120℃; under 120 Torr;	83%

...Expand

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 143101-96-6
(3S,5S,8S,9S,10S,13R,14S,16R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-16-carboxylic acid ethyl ester

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride at 120℃; under 120 Torr;	80%

...Expand

: 7148-51-8
5α-androst-16-en-3β-ol

A: 50588-44-8
5α-androsta-2,16-diene

B: 3α-fluoro-5α-androst-16-ene

Conditions

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0 - 5℃; for 1h;	A 20% B 69%

: 7148-51-8
5α-androst-16-en-3β-ol

: C16H20Cl3NO10

A: C26H40O7

B: C26H40O7

Conditions

Conditions	Yield
Stage #1: 5α-androst-16-en-3β-ol; C16H20Cl3NO10 With boron trifluoride diethyl etherate In dichloromethane at -15℃; for 16h; Molecular sieve; Stage #2: With water; sodium hydroxide In methanol for 1h; Overall yield = 67 %;	A 60% B n/a

...Expand

: 7148-51-8
5α-androst-16-en-3β-ol

: 1224-93-7, 7657-50-3, 7753-89-1, 10085-14-0, 15360-52-8, 15360-53-9, 36216-01-0, 36216-02-1, 1224-92-6
5α-androstan-3β-ol

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;

: 7148-51-8
5α-androst-16-en-3β-ol

: 14339-58-3
5α-androstanetriol-(3β.16α.17α)

Conditions

Conditions	Yield
With pyridine; osmium(VIII) oxide; diethyl ether Schuetteln des Reaktionsprodukts mit wss. KOH und Mannit;

: 7148-51-8
5α-androst-16-en-3β-ol

: 108-24-7
acetic anhydride

: 72203-76-0
5α-androst-16-en-3β-yl acetate

Conditions

Conditions	Yield
With pyridine

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 142794-26-1
(3S,5S,8S,9S,10S,13R,14S,16R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-16-carbaldehyde

Conditions

Conditions	Yield
With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; triethylamine In benzene at 120℃; under 90007.2 Torr;	72 % Spectr.

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 67-63-0
isopropyl alcohol

: 143101-97-7
(3S,5S,8S,9S,10S,13R,14S,16R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-16-carboxylic acid isopropyl ester

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride at 100℃; under 80 Torr;	69 % Chromat.

...Expand

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 67-63-0
isopropyl alcohol

: 143101-98-8
(3S,5S,8S,9S,10S,13R,14S,16R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-16-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride at 100℃; under 80 Torr;	80 % Chromat.

...Expand

: 7148-51-8
5α-androst-16-en-3β-ol

A: 5856-11-1
5alpha-Androstane-3beta,17alpha-diol

B: 22630-49-5
3β,16α-dihydroxy-5α-androstane

Conditions

Conditions	Yield
With sodium hydroxide; borane; dihydrogen peroxide 1.) THF, 4 h, 2.) overnight; Yield given; Multistep reaction;	A n/a B 1.58 g
With sodium hydroxide; borane; dihydrogen peroxide 1.) THF, 4 h, 2.) overnight; Yield given; Multistep reaction;	A 1.17 g B n/a

: 7148-51-8
5α-androst-16-en-3β-ol

: 16α,17α-epoxy-5α-androstane-3β-ol

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) 0 deg C, 10 min, 2.) room temperature, 2 h;	1.1 g
With 3-chloro-benzenecarboperoxoic acid In chloroform

: 109-83-1
(2-hydroxyethyl)(methyl)amine

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

A: 1224-93-7, 7657-50-3, 7753-89-1, 10085-14-0, 15360-52-8, 15360-53-9, 36216-01-0, 36216-02-1, 1224-92-6
5α-androstan-3β-ol

B: 3β-hydroxy-16α(β)-[N,N-(methyl, 2-hydroxyethylamino)methyl]-5α-androstane

C: (3S,5S,8S,9S,10S,13R,14S)-16-[1-[(2-Hydroxy-ethyl)-methyl-amino]-meth-(Z)-ylidene]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol

Conditions

Conditions	Yield
With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; hydrogen In benzene at 120℃; under 60800 Torr; for 6h; Carbonylation; condensation; hydrogenation;	A 13.7 % Chromat. B 78.4 % Chromat. C 7.8 % Chromat.

...Expand

: 96-20-8, 13054-87-0
2-aminobutanol

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

A: 1224-93-7, 7657-50-3, 7753-89-1, 10085-14-0, 15360-52-8, 15360-53-9, 36216-01-0, 36216-02-1, 1224-92-6
5α-androstan-3β-ol

B: (3S,5S,8S,9S,10S,13R,14S)-16-[(1-Hydroxymethyl-propylamino)-methyl]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol

Conditions

Conditions	Yield
With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; hydrogen In benzene at 120℃; under 60800 Torr; for 6h; Carbonylation; condensation; hydrogenation;	A 7.4 % Chromat. B 92.6 % Chromat.

...Expand

: 16369-21-4
N-(2-hydroxyethyl)-N-propylamine

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

A: 1224-93-7, 7657-50-3, 7753-89-1, 10085-14-0, 15360-52-8, 15360-53-9, 36216-01-0, 36216-02-1, 1224-92-6
5α-androstan-3β-ol

B: (3S,5S,8S,9S,10S,13R,14S)-16-[1-[(2-Hydroxy-ethyl)-propyl-amino]-meth-(Z)-ylidene]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol

C: (3S,5S,8S,9S,10S,13R,14S)-16-{[(2-Hydroxy-ethyl)-propyl-amino]-methyl}-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol

Conditions

Conditions	Yield
With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; hydrogen In benzene at 120℃; under 60800 Torr; for 6h; Carbonylation; condensation; hydrogenation;	A 6.5 % Chromat. B 4.4 % Chromat. C 89.0 % Chromat.

...Expand

: 201230-82-2
carbon monoxide

: 7148-51-8
5α-androst-16-en-3β-ol

: 156-87-6
propan-1-ol-3-amine

A: 1224-93-7, 7657-50-3, 7753-89-1, 10085-14-0, 15360-52-8, 15360-53-9, 36216-01-0, 36216-02-1, 1224-92-6
5α-androstan-3β-ol

B: 3β-hydroxy-16α(β)-[N-(3-hydroxypropylamino)methyl]-5α-androstane

Conditions

Conditions	Yield
With di-μ-chlorobis(norbornadiene)dirhodium(I); tributylphosphine; hydrogen In benzene at 120℃; under 60800 Torr; for 6h; Carbonylation; condensation; hydrogenation;	A 8.2 % Chromat. B 91.8 % Chromat.

...Expand

: 110-86-1
pyridine

: 60-29-7
diethyl ether

: 7148-51-8
5α-androst-16-en-3β-ol

OsO4: OsO4

: 14339-58-3
5α-androstanetriol-(3β.16α.17α)

Conditions

Conditions	Yield
Schuetteln des Reaktionsprodukts mit wss. KOH und Mannit;

...Expand

: 7148-51-8
5α-androst-16-en-3β-ol

: 7657-53-6
3β,16β-dihydroxy-5α-androstane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) borane, 2.) aq. NaOH, H2O2 / 1.) THF, 4 h, 2.) overnight 2: 1 g / CrO3 / acetone / 0.5 h / 0 deg C to room temperature 3: 0.85 g / NaBH4 / methanol / 0.67 h / 0 °C View Scheme

: 7148-51-8
5α-androst-16-en-3β-ol

: 24317-68-8
11α,16β-dihydroxy-5α-androstane-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) borane, 2.) aq. NaOH, H2O2 / 1.) THF, 4 h, 2.) overnight 2: 1 g / CrO3 / acetone / 0.5 h / 0 deg C to room temperature 3: 0.85 g / NaBH4 / methanol / 0.67 h / 0 °C 4: 4.5 percent / Cephalosporium aphidicola in shake culture / ethanol / 168 h View Scheme

: 7148-51-8
5α-androst-16-en-3β-ol

: 1035-71-8
5α-androstane-3,16-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) borane, 2.) aq. NaOH, H2O2 / 1.) THF, 4 h, 2.) overnight 2: 1 g / CrO3 / acetone / 0.5 h / 0 deg C to room temperature View Scheme

5alpha-Androst-16-en-3beta-ol Specification

The IUPAC name of 5alpha-Androst-16-en-3beta-ol is (3S,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol. With the CAS registry number 7148-51-8, it is also named as 16,(5-alpha)-Androsten-3-beta-ol. The product's categories are Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Steroids. It is a metabolite of 16-Androstene.

The other characteristics of 5alpha-Androst-16-en-3beta-ol can be summarized as: (1)ACD/LogP: 5.88; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.88; (4)ACD/LogD (pH 7.4): 5.88; (5)ACD/BCF (pH 5.5): 17447; (6)ACD/BCF (pH 7.4): 17447; (7)ACD/KOC (pH 5.5): 37827.77; (8)ACD/KOC (pH 7.4): 37827.77; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.54; (13)Molar Refractivity: 82.96 cm³; (14)Molar Volume: 264.4 cm³; (15)Polarizability: 32.89×10^-24 cm³; (16)Surface Tension: 41.1 dyne/cm; (17)Enthalpy of Vaporization: 71.9 kJ/mol; (18)Vapour Pressure: 4E-07 mmHg at 25°C; (19)Exact Mass: 274.229666; (20)MonoIsotopic Mass: 274.229666; (21)Topological Polar Surface Area: 20.2; (22)Heavy Atom Count: 20; (23)Complexity: 428; (24)Defined Atom StereoCenter Count: 7.

People can use the following data to convert to the molecule structure.
1. SMILES:O[C@@H]4C[C@@H]3CC[C@H]2[C@H]1[C@@](/C=C\C1)(CC[C@@H]2[C@@]3(C)CC4)C
2. InChI:InChI=1/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
3. InChIKey:KRVXMNNRSSQZJP-LOVVWNRFBX

Product Name

16,(5-ALPHA)-ANDROSTEN-3-BETA-OL

Synthetic route

5alpha-Androst-16-en-3beta-ol Specification

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