methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate

Base Information

• Chemical Name: methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate
• CAS No.: 133379-87-0
• Molecular Formula: C₂₀H₂₂O₃
• Molecular Weight: 310.393
• Mol file: 133379-87-0.mol

Synonyms:methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate

Chemical Property of methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate

There total 4 articles about methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate 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:

allyltributylstanane (24850-33-7) + methyl (+/-)-(2S*,3S*)-2-iodo-3-benzyloxy-3-phenylpropanoate (133379-86-9) → methyl (+/-)-(2R*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate (133379-87-0) + methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate (133379-87-0)

Guidance literature:

With triethyl borane; In toluene; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)71209-3

Reference yield:

allyltributylstanane (24850-33-7) + methyl (+/-)-(2S*,3S*)-2-iodo-3-benzyloxy-3-phenylpropanoate (133379-86-9) → methyl (+/-)-(2R*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate (133379-87-0) + methyl (+/-)-(2S*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate (133379-87-0)

Guidance literature:

With triethyl borane; In toluene; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)71209-3

Reference yield:

Methyl cinnamate (103-26-4,1754-62-7) → methyl (+/-)-(2R*,3S*)-2-[propen-3-yl]-3-benzyloxy-3-phenylpropanoate (133379-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / I₂; AgNO₃ / 24 h / 25 °C

2: Et₃B / CH₂Cl₂; hexane / -78 °C

With triethyl borane; iodine; silver nitrate; In hexane; dichloromethane; 1: Addition / 2: Substitution;

DOI:10.1139/v00-074

upstream raw materials:

allyltributylstanane

methyl (+/-)-(2S*,3S*)-2-iodo-3-benzyloxy-3-phenylpropanoate

Methyl cinnamate