(R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester

Base Information

• Chemical Name: (R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester
• CAS No.: 94349-16-3
• Molecular Formula: C₃₁H₃₇NO₅
• Molecular Weight: 503.638
• Mol file: 94349-16-3.mol

Synonyms:(R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester

Chemical Property of (R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester

There total 1 articles about (R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl 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:

4-((2R,3S)-3-{(1R,2R)-1,2-Bis-benzyloxy-3-[benzyl-(toluene-4-sulfonyl)-amino]-propyl}-oxiranyl)-butyric acid ethyl ester → (R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester (94349-16-3)

Guidance literature:

With sodium naphthalenide; In 1,2-dimethoxyethane; at -60 ℃; for 0.5h;

DOI:10.1021/jo00203a039

Reference yield:

(R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester (94349-16-3) → swainsonine (72741-87-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 79 percent / Dibal / toluene / 2 h / 0 °C

3: 100 percent / MsCl, Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

4: 100 percent / HCO₂H / Pd black / methanol / 18 h / Ambient temperature

5: 84 percent / Dowex 50W-X₈ / methanol / 24 h

With formic acid; Dowex 50W-X₈; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; palladium; In methanol; dichloromethane; toluene;

DOI:10.1021/jo00203a039

Reference yield:

(R)-4-((2R,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-hydroxy-butyric acid ethyl ester (94349-16-3) → (R)-4-((2S,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol (94349-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 79 percent / Dibal / toluene / 2 h / 0 °C

With diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo00203a039

Downstream raw materials:

swainsonine

(R)-4-((2S,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol