Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine

Base Information

• Chemical Name: Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine
• CAS No.: 203795-96-4
• Molecular Formula: C₃₈H₆₀N₁₀O₃
• Molecular Weight: 704.96
• Mol file: 203795-96-4.mol

Synonyms:Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine

Chemical Property of Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine

There total 10 articles about Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine 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: 93.0%

benzyl-methyl-amine (103-67-3) + Methanesulfonic acid (R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl ester → Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine (203795-96-4)

Guidance literature:

benzyl-methyl-amine; Methanesulfonic acid (R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl ester; at 80 ℃; Heating / reflux;

benzyl-methyl-amine; at 80 ℃; Heating / reflux;

Reference yield:

3β,7α,12α-trihydroxy-5β-cholan-24-oic acid methyl ester (28050-54-6) → Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine (203795-96-4)

Guidance literature:

Multi-step reaction with 10 steps

1: LiAlH₄ / tetrahydrofuran

2: Et₃N / dimethylformamide

3: NaH / tetrahydrofuran

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH

5: NaBH₄

6: Et₃N / CH₂Cl₂

7: NaN₃ / dimethylsulfoxide

8: TsOH / methanol

9: Et₃N / CH₂Cl₂

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; dimethylsulfide; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja973881r

Reference yield:

2-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-Bis-(2-hydroxy-ethoxy)-10,13-dimethyl-17-((R)-1-methyl-4-trityloxy-butyl)-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-ethanol (203795-91-9) → Benzyl-methyl-{(R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tris-(2-azido-ethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentyl}-amine (203795-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂

2: NaN₃ / dimethylsulfoxide

3: TsOH / methanol

4: Et₃N / CH₂Cl₂

With sodium azide; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja973881r

upstream raw materials:

benzyl-methyl-amine

3β,7α,12α-trihydroxy-5β-cholan-24-oic acid methyl ester

2-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7-Bis-(2-hydroxy-ethoxy)-10,13-dimethyl-17-((R)-1-methyl-4-trityloxy-butyl)-hexadecahydro-cyclopenta[a]phenanthren-12-yloxy]-ethanol

(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-allyloxy-10,13-dimethyl-17-((R)-1-methyl-4-trityloxy-butyl)-hexadecahydro-cyclopenta[a]phenanthrene

Refernces

• 1、 Li, Chunhong,Peters, Adam S.,Meredith, Erik L.,Allman, Glenn W.,Savage, Paul B.. "Design and Synthesis of Potent Sensitizers of Gram-Negative Bacteria Based on a Cholic Acid Scaffolding". . p. 2961 - 2962. Retrieved 2007/10/03.