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Methyl 3-oxo-4-androstene-17beta-carboxylate is a synthetic androgen steroid that functions as a derivative of the male sex hormone testosterone. It is designed to emulate the effects of testosterone, primarily promoting muscle growth and strength. Methyl 3-oxo-4-androstene-17beta-carboxylate is part of the anabolic steroids class and is frequently utilized in the bodybuilding and fitness industry as a performance-enhancing drug, despite being associated with various health risks and legal restrictions.

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  • 2681-55-2 Structure
  • Basic information

    1. Product Name: Methyl 3-oxo-4-androstene-17beta-carboxylate
    2. Synonyms: METHYL 4-ANDROSTEN-3-ONE-17BETA-CARBOXYLINATE;Methyl-3-oxo-4-androstene-17beta-carboxylate;(8S,9S,10R,13S,14S,17S)-3-keto-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylic acid methyl ester;methyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylate;Methyl-3-xox-4-androsten-17β-carboxylate;Methyl 3-Oxo-4-Androsten-17β-Carboxylate;(8S,9S,10R,13S,14S,17S)-Methyl 10,13-diMethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate;Methyl-3-oxo-4-androsten-17b-carboxylate
    3. CAS NO:2681-55-2
    4. Molecular Formula: C21H30O3
    5. Molecular Weight: 330.46
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 2681-55-2.mol
  • Chemical Properties

    1. Melting Point: 130-131 °C
    2. Boiling Point: 441.8 °C at 760 mmHg
    3. Flash Point: 191.5 °C
    4. Appearance: /
    5. Density: 1.12 g/cm3
    6. Vapor Pressure: 5.28E-08mmHg at 25°C
    7. Refractive Index: 1.54
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: Methyl 3-oxo-4-androstene-17beta-carboxylate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Methyl 3-oxo-4-androstene-17beta-carboxylate(2681-55-2)
    12. EPA Substance Registry System: Methyl 3-oxo-4-androstene-17beta-carboxylate(2681-55-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 2681-55-2(Hazardous Substances Data)

2681-55-2 Usage

Uses

Used in Bodybuilding and Fitness Industry:
Methyl 3-oxo-4-androstene-17beta-carboxylate is used as a performance-enhancing drug for [the purpose of] increasing muscle mass and physical strength. It is favored by athletes and bodybuilders seeking to improve their physical performance and appearance, although its use is often illegal and banned by many sports organizations due to the potential for serious side effects.
Used in Pharmaceutical Research:
While not explicitly mentioned in the provided materials, due to its structural similarity to testosterone, Methyl 3-oxo-4-androstene-17beta-carboxylate may also be used as a research compound in the development of pharmaceuticals targeting muscle wasting diseases or conditions where muscle growth is impaired. Its application in this context would be for [the purpose of] understanding and potentially treating such conditions more effectively.

Check Digit Verification of cas no

The CAS Registry Mumber 2681-55-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,8 and 1 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2681-55:
(6*2)+(5*6)+(4*8)+(3*1)+(2*5)+(1*5)=92
92 % 10 = 2
So 2681-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O3/c1-20-10-8-14(22)12-13(20)4-5-15-16-6-7-18(19(23)24-3)21(16,2)11-9-17(15)20/h12,15-18H,4-11H2,1-3H3/t15?,16?,17?,18-,20+,21+/m1/s1

2681-55-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 3-oxo-4-androstene-17beta-carboxylate

1.2 Other means of identification

Product number -
Other names methyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2681-55-2 SDS

2681-55-2Synthetic route

17β-androstane-4-ene-3-keto-17-formaldehyde
6247-91-2

17β-androstane-4-ene-3-keto-17-formaldehyde

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium iodide In methanol at 20℃; for 6.5h; Reagent/catalyst; Reflux;93%
androst-4-en-3-one-17β-carboxylic acid
302-97-6

androst-4-en-3-one-17β-carboxylic acid

temozolomide
85622-93-1

temozolomide

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 60℃; for 4h; Sealed tube;89%
methyl 5-androsten-3β-ol-17β-carboxylate
85541-82-8, 95119-09-8, 7254-03-7

methyl 5-androsten-3β-ol-17β-carboxylate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide In toluene87%
With aluminum isopropoxide In cyclohexanone; toluene at 110℃; for 3h; Oppenauer Oxidation; Inert atmosphere;82%
With aluminum isopropoxide In cyclohexanone; toluene for 4h; Oxidation; Oppennauer oxidation; Heating;70.62%
tert-butyl methyl ether
1634-04-4

tert-butyl methyl ether

androst-4-en-3-one-17β-carboxylic acid
302-97-6

androst-4-en-3-one-17β-carboxylic acid

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;79%
methanol
67-56-1

methanol

C24H31NO2

C24H31NO2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 18h; Sealed tube; chemoselective reaction;64%
methanol
67-56-1

methanol

17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion
121329-22-4

17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion
121329-29-1

(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion

Conditions
ConditionsYield
With sodium azide for 22h; Ambient temperature;A 48%
B 10%
17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion
121329-22-4

17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion
121329-29-1

(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion

Conditions
ConditionsYield
With sodium azide In methanol at 50℃; for 1.5h;A 8%
B 39%
androst-4-en-3-one-17β-carboxylic acid
302-97-6

androst-4-en-3-one-17β-carboxylic acid

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With diethyl ether
methyl 3-oxo-androst-1,4-diene-17β-carboxylate
111497-46-2

methyl 3-oxo-androst-1,4-diene-17β-carboxylate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Hydrogenation;
2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester
114127-58-1

2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

3-oxo-5β-androst-1-ene-17β-carboxylic acid methyl ester
111407-58-0

3-oxo-5β-androst-1-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With acetone; sodium iodide Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol;
methyl 5-androsten-3β-ol-17β-carboxylate
85541-82-8, 95119-09-8, 7254-03-7

methyl 5-androsten-3β-ol-17β-carboxylate

cyclohexanone
108-94-1

cyclohexanone

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With aluminum isopropoxide; toluene
methyl 5-androsten-3β-ol-17β-carboxylate
85541-82-8, 95119-09-8, 7254-03-7

methyl 5-androsten-3β-ol-17β-carboxylate

cyclohexanone
108-94-1

cyclohexanone

aluminum isopropoxide
555-31-7

aluminum isopropoxide

toluene
108-88-3

toluene

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester
114127-58-1

2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

3-oxo-androst-1-ene-17β-carboxylic acid methyl ester

3-oxo-androst-1-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With acetone; sodium iodide Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol;
3β,5-dihydroxy-21-nor-5β-pregnanoic acid-(20)-methyl ester
55955-57-2

3β,5-dihydroxy-21-nor-5β-pregnanoic acid-(20)-methyl ester

acetic acid
64-19-7

acetic acid

chromium (VI)-oxide

chromium (VI)-oxide

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts mit Essigsaeure;
17β-acetoxy-3β-hydroxy-3α-methylandrost-4-ene

17β-acetoxy-3β-hydroxy-3α-methylandrost-4-ene

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

17β-acetoxy-3β,4β-epoxy-5β-hydroxy-3α-methylandrostane

17β-acetoxy-3β,4β-epoxy-5β-hydroxy-3α-methylandrostane

Conditions
ConditionsYield
With chromium(VI) oxide In acetone at 20℃;A 50 mg
B 290 mg
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cesium fluoride / dimethylformamide / 24 h / 20 °C
2: 3.1 g / cyclohexanone; aluminium isopropoxide / toluene / Heating
View Scheme
Multi-step reaction with 2 steps
1: 82 percent / p-toluenesulfonic acid / 5 h / Heating
2: 87 percent / Al(i-PrO)3, cyclohexanone / toluene
View Scheme
Multi-step reaction with 2 steps
1: Reaktion ueber mehrere Stufen
2: diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 3 h / Reflux
2: aluminum isopropoxide / toluene; cyclohexanone / 3 h / 110 °C / Inert atmosphere
View Scheme
Pregnenolone
145-13-1

Pregnenolone

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: I2 / 1.5 h / Heating
2: methanol / 1 h / Heating
3: 70.62 percent / Al(i-PrO)3 / cyclohexanone; toluene / 4 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: I2 / 1 h / Heating
2: methanol / 1 h / Heating
3: 1.) Al(i-PrO)3, 2.) Supercel, Darco KB / 1.) toluene, cyclohexanone, reflux, 1 h, 2.) toluene, cyclohexanone, water, 15 min
View Scheme
Multi-step reaction with 3 steps
1: iodine / 1.5 h / 90 °C / Inert atmosphere; Reflux
2: sodium methylate / 16 h / Inert atmosphere; Reflux
3: cyclohexanone; aluminum isopropoxide / toluene / 4 h / Reflux; Inert atmosphere
View Scheme
pregnenolone 21-pyridinium iodide
73672-02-3

pregnenolone 21-pyridinium iodide

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 1 h / Heating
2: 70.62 percent / Al(i-PrO)3 / cyclohexanone; toluene / 4 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: methanol / 1 h / Heating
2: 1.) Al(i-PrO)3, 2.) Supercel, Darco KB / 1.) toluene, cyclohexanone, reflux, 1 h, 2.) toluene, cyclohexanone, water, 15 min
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / 16 h / Inert atmosphere; Reflux
2: cyclohexanone; aluminum isopropoxide / toluene / 4 h / Reflux; Inert atmosphere
View Scheme
Pregnenolone acetate
1778-02-5

Pregnenolone acetate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaOBr, 2.) HCl / 1.) dioxane, water
2: 82 percent / p-toluenesulfonic acid / 5 h / Heating
3: 87 percent / Al(i-PrO)3, cyclohexanone / toluene
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hypobromide / water; 1,4-dioxane / 3 h / 5 - 8 °C
1.2: 0.25 h / Reflux
1.3: 24 h / 5 - 90 °C
2.1: sulfuric acid / 3 h / Reflux
3.1: aluminum isopropoxide / toluene; cyclohexanone / 3 h / 110 °C / Inert atmosphere
View Scheme
21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68.3 percent / H2O2, 0.2N NaOH / hemin / methanol / 4 h / 20 °C
View Scheme
21-(Acetylthio)-17-hydroxy-4-pregnen-3,20-dion
113926-62-8

21-(Acetylthio)-17-hydroxy-4-pregnen-3,20-dion

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / DMAP / bis-(2-methoxy-ethyl) ether / 17 h / Ambient temperature
2: 48 percent / NaN3 / 22 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 73 percent / DMAP / bis-(2-methoxy-ethyl) ether / 17 h / Ambient temperature
2: 8 percent / NaN3 / methanol / 1.5 h / 50 °C
View Scheme
methyl 3-oxo-5β-androstane-17β-carboxylate
50305-74-3

methyl 3-oxo-5β-androstane-17β-carboxylate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine
2: NaI; acetone / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol
View Scheme
Multi-step reaction with 2 steps
1: bromine
2: NaI; acetone / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol
View Scheme
methyl 5-androsten-3β-ol-17β-carboxylate
85541-82-8, 95119-09-8, 7254-03-7

methyl 5-androsten-3β-ol-17β-carboxylate

A

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B

methyl 3-oxo-androst-4,6-diene-17β-carboxylate
116934-48-6

methyl 3-oxo-androst-4,6-diene-17β-carboxylate

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0 - 20℃; Overall yield = 75 %;
Androstenedione
63-05-8

Androstenedione

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 5 h / 5 °C / Inert atmosphere
2: n-butyllithium / 2-methyltetrahydrofuran / 6 h / -60 - -45 °C / Inert atmosphere
3: tert.-butylhydroperoxide; potassium iodide / methanol / 6.5 h / 20 °C / Reflux
View Scheme
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

androst-4-en-3-one-17β-carboxylic acid
302-97-6

androst-4-en-3-one-17β-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 5h; Hydrolysis; Heating;100%
With potassium hydroxide In ethanol; water95%
With potassium hydroxide In methanol; water for 3h; Inert atmosphere; Reflux;89%
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate
119169-85-6

Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate

Conditions
ConditionsYield
With phosphorus tribromide In acetic acid for 21h; Ambient temperature;85%
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester
150723-49-2

3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.5h;82%
With sodium tetrahydroborate
With sodium tetrahydroborate In methanol at 0℃; Reduction;
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

methyl 3-oxo-androst-1,4-diene-17β-carboxylate
111497-46-2

methyl 3-oxo-androst-1,4-diene-17β-carboxylate

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 48h; Reflux;81.2%
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

methyl 3-oxo-androst-4,6-diene-17β-carboxylate
116934-48-6

methyl 3-oxo-androst-4,6-diene-17β-carboxylate

Conditions
ConditionsYield
With chloranil In chloroform; tert-butyl alcohol70%
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

methyl iodide
74-88-4

methyl iodide

C23H34O3
1609387-14-5

C23H34O3

Conditions
ConditionsYield
Stage #1: 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
63%
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

A

androsta-3,5-diene-17β-carboxylic acid methyl ester
23737-99-7

androsta-3,5-diene-17β-carboxylic acid methyl ester

B

3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester
150723-49-2

3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

2ξ,6ξ-dibromo-3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
423166-44-3

2ξ,6ξ-dibromo-3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With bromine
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

A

methyl 3β-hydroxy-5α-androstane-17β-carboxylate
10002-85-4

methyl 3β-hydroxy-5α-androstane-17β-carboxylate

B

3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester
74464-95-2

3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With methanol; palladium anschliessend Hydrierung an Platin in Methanol und Essigsaeure; Isolierung von Digitonin;
With methanol; palladium anschliessend Hydrierung an Platin in Methanol und Essigsaeure;
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

3α-acetoxy-5β-androstane-17β-carboxylic acid methyl ester
74497-93-1

3α-acetoxy-5β-androstane-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
With ethanol; alkaline solution; nickel Hydrogenation.Behandlung der neutralen Anteile des Reaktionsprodukts mit Acetanhydrid und Pyridin;
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

17β-methoxycarbonyl-5-oxo-3,5-seco-A-nor-androstan-3-oic acid
92472-33-8

17β-methoxycarbonyl-5-oxo-3,5-seco-A-nor-androstan-3-oic acid

Conditions
ConditionsYield
With chloroform; ozone Behandeln des Reaktionsprodukts mit wss. Essigsaeure und anschliessendes Erwaermen mit Zink;
With potassium permanganate; sodium periodate; sodium carbonate In water; tert-butyl alcohol Heating;
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

acetic anhydride
108-24-7

acetic anhydride

acetyl chloride
75-36-5

acetyl chloride

3-acetoxy-androstadiene-(3.5)-carboxylic acid-(17β)-methyl ester
911663-11-1

3-acetoxy-androstadiene-(3.5)-carboxylic acid-(17β)-methyl ester

Conditions
ConditionsYield
at 100 - 140℃;
Methyl formate
107-31-3

Methyl formate

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

(8S,9S,10R,13S,14S,17S)-2-[1-Hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methyl ester
138091-50-6

(8S,9S,10R,13S,14S,17S)-2-[1-Hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium methylate
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

17β-androstane-4-ene-3-keto-17-formaldehyde
6247-91-2

17β-androstane-4-ene-3-keto-17-formaldehyde

Conditions
ConditionsYield
With lithium aluminium tetrahydride 1.) THF, room temperature, 1 h, 0 deg C; 2.) oxidation; Yield given. Multistep reaction;
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

17β-carbomethoxyandrost-4-ene
119169-67-4

17β-carbomethoxyandrost-4-ene

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 2h; Reduction;
methanol
67-56-1

methanol

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
2681-55-2

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

palladium

palladium

A

methyl 3β-hydroxy-5α-androstane-17β-carboxylate
10002-85-4

methyl 3β-hydroxy-5α-androstane-17β-carboxylate

B

3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester
74464-95-2

3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester

Conditions
ConditionsYield
anschliessend Hydrierung an Platin in Essigsaeure enthaltendem Methanol;

2681-55-2Relevant articles and documents

Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions

Chen, Hang,Chen, Dong-Huang,Huang, Pei-Qiang

, p. 370 - 376 (2020/03/03)

N-Acylpyrrole-type amides are a class of versatile building blocks in asymmetric synthesis. We report that by employing Ni(COD)2/2,2′-bipyridine (5 mol%) catalytic system, the direct, catalytic alcoholysis of N-acylpyrrole-type aromatic and aliphatic amides with both primary and secondary alcohols can be achieved efficiently under very mild conditions (rt, 1 h) even at gram scale. By increasing the catalyst loading to 10 mol%, prolonging reaction time (18 h), and/or elevating reaction temperature to 50 °C/80 °C, the reaction could be extended to both complex and hindered N-acylpyrroles as well as to N-acylpyrazoles, Nacylindoles, and to other (functionalized) primary and secondary alcohols. In all cases, only 1.5 equiv. of alcohol were used. The value of the method has been demonstrated by the racemization-free, catalytic alcoholysis of chiral amides yielded from other asymmetric methodologies.

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Svec, Riley L.,Hergenrother, Paul J.

supporting information, p. 1857 - 1862 (2019/12/27)

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Method for synthesizing methyl 3-oxo-4-androstene-17beta-carboxylate

-

Paragraph 0013; 0036; 0037; 0038; 0045; 0046; 0047, (2019/03/29)

The invention discloses a method for synthesizing methyl 3-oxo-4-androstene-17beta-carboxylate. The method comprises the following steps: (a) performing etherification protection on 3-site keto groupwith sterol fermentation broth androst-4-allyl-3,17-diketone as a starting material to obtain a compound shown by the formula 2 as shown in the specification; (b) performing Witt reaction on 3-site keto of the compound shown by the formula 2, and performing hydrolysis rearrangement to obtain a compound shown by the formula 3 as shown in the specification; and (c) performing esterification on the compound shown by the formula 3, and then collecting methyl 3-oxo-4-androstene-17beta-carboxylate shown by the formula 1 as shown in the specification from reaction products. The method disclosed in the invention has the advantages that raw material sources are stable, the pollution is less, the environmental protection is achieved and the price is low, therefore, the synthesis method is low in cost, easy, convenient and fast in process and more environmentally-friendly. The response equation is shown in the specification.

Protection of COOH and OH groups in acid, base and salt free reactions

Zhu, Xiaotao,Qian, Bo,Wei, Rongbiao,Huang, Jian-Dong,Bao, Hongli

supporting information, p. 1444 - 1447 (2018/04/12)

We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

Effective and mild method for converting 3β-hydroxysteroids to 3-keto steroids via DDQ/TEMPO

Zhang, Wu,Pan, Dan,Wu, Aiqun,Shen, Liqun

, p. 16 - 20 (2015/03/04)

A mild and efficient oxidation of 3β-hydroxysteroids to the corresponding 3-keto steroids can be carried out at room temperature, using DDQ in the presence of catalytic TEMPO. Oxidation of saturated 3β-hydroxysteroids gave the corresponding ketones in excellent yield. The 5-unsaturated 3β-hydroxysteroids are oxidized selectively to 4-en-3-one or 4,6-diene-3-one derivatives according to the amount of DDQ in reaction. This is a good method for the synthesis of 4,6-diene-3-one from the corresponding 3β-hydroxy-5-ene steroids. Meanwhile, configurations of the oxidation compounds 2a, 2b, 3b, 2c, 2f and 2g were identified by X-ray diffraction. A possible mechanism is presented and discussed.

Design and diastereoselective synthesis of C-2,C-20-diaryl steroidal derivatives

Rey, Jullien,O'Riordan, Timothy J. C.,Hu, Haipeng,Snyder, James P.,White, Andrew J. P.,Barrett, Anthony G. M.

, p. 3781 - 3794 (2012/10/08)

A novel and efficient synthetic strategy to access unique C-2 substituted steroid analogues 3 and 4 is described. The unusual C-2 aryl ether analogues 3 were shown to act as virtual antagonists of LRH-1 and were prepared as single diastereoisomers, employing a fifteen-step sequence from pregnenolone (9). The key steps include the stereoconvergent nucleophilic displacement of an epimeric mixture of 3-keto 2-bromo steroids, chemoselective carbonylation of an enol triflate and conversion of a thiopyridyl ester into an aryl ketone. The related C-2 benzyl analogues 4 were prepared in a similar manner. Starting from pregnenolone, a diastereoselective fifteen-step synthesis was developed to access novel C-2-substituted steroid analogues. A range of C-2 benzyl and aryl ether analogues were prepared to probe their efficacy as antagonists of the nuclear receptor LRH-1. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

The first synthesis of Krempene B

Shen, Li-Qun,Huang, Su-Yu,Tang, Yong,Lei, Fu-Hou

, p. 1398 - 1402 (2013/01/15)

The synthesis of Krempene B, which can be isolated from the marine soft coral Cladiella krempfi, is achieved in 23.9% overall yield from commercially available 3β-acetoxy-5-pregnen-20-one by 11 steps. Key transformations include the dienone-phenol rearrangement of steroids and Wittig reaction.

The oxidation of 3-hydroxy-3-methyl-Δ4-steroids by chromium trioxide

Uyanik, Cavit,Hanson, James R.,Hitchcock, Peter B.

, p. 795 - 797 (2007/10/03)

Oxidation of the allylic tertiary alcohols of 3-hydroxy-3-methyl-Δ 4-steroids by chromium trioxide in sulfuric acid leads to C-C bond fission together with the formation of a 3-methylestra-1,3,5(10)-triene from a 19-nor steroid and a 3β,4β-epoxy-5β-hydroxy compound from an androstane; the structure of the hydroxy-epoxide was established by X-ray crystallography.

Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents

Xia, Peng,Yang, Zheng-Yu,Xia, Yi,Zheng, Yun-Qing,Cosentino, L.Mark,Lee, Kuo-Hsiung

, p. 1907 - 1911 (2007/10/03)

In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 μM and 300, respectively.

Steroidal Aphidicolin Analogues Derived from Pregnenolone

Hanson, James R.,Yildirim, Kudret

, p. 2975 - 2991 (2007/10/03)

The converision of pregnenolone into the 3β,5α-, 3α,5α-, 4β,5α-, 3β,4α, 3α,4β- and 3α,4α-dihydroxy derivatives of 17β-hydroxymethyl-5α-androstane as steroidal analogues of the diterpenoid DNA polymerase α inhibitor, aphidicolin, is described.

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