Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Base Information

• Chemical Name: Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester
• CAS No.: 756852-32-1
• Molecular Formula: C₃₄H₅₁NO₅
• Molecular Weight: 553.783
• Mol file: 756852-32-1.mol

Synonyms:Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Chemical Property of Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

There total 3 articles about Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

N-benzyloxyamine (622-33-3) + 23-oxo-24-nor-5β-cholane-3α,7α-diyl diacetate (202462-10-0) → Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (756852-32-1)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; at 20 ℃; for 48h; pH=5;

DOI:10.1021/jm049904b

Reference yield:

24-nor-5β-chol-22-ene-3α,7α-diol diacetate (57071-90-6) → Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (756852-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*THF / tetrahydrofuran / 3 h / 20 °C

1.2: 63 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

2.1: PCC / CH₂Cl₂ / 12 h / 20 °C

3.1: 42 percent / sodium cyanoborohydride; 2 N aq. HCl / methanol / 48 h / 20 °C / pH 5

With hydrogenchloride; borane-THF; sodium cyanoborohydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm049904b

Reference yield:

3α,7α-diacetoxy-23-hydroxy-24-nor-5β-cholane (210490-43-0) → Acetic acid (3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-acetoxy-17-((R)-3-benzyloxyamino-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (756852-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: PCC / CH₂Cl₂ / 12 h / 20 °C

2: 42 percent / sodium cyanoborohydride; 2 N aq. HCl / methanol / 48 h / 20 °C / pH 5

With hydrogenchloride; sodium cyanoborohydride; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/jm049904b

upstream raw materials:

N-benzyloxyamine

23-oxo-24-nor-5β-cholane-3α,7α-diyl diacetate

24-nor-5β-chol-22-ene-3α,7α-diol diacetate

3α,7α-diacetoxy-23-hydroxy-24-nor-5β-cholane