(S)-2-acetoxypropionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-acetoxypropionic acid benzyl ester
• CAS No.: 151838-56-1
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.241
• Mol file: 151838-56-1.mol

Synonyms:(S)-2-acetoxypropionic acid benzyl ester

Chemical Property of (S)-2-acetoxypropionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of (S)-2-acetoxypropionic acid benzyl ester

There total 4 articles about (S)-2-acetoxypropionic acid benzyl 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: 97.0%

benzyl (S)-Lactate (56777-24-3) + acetic anhydride (108-24-7) → (S)-2-acetoxypropionic acid benzyl ester (151838-56-1)

Guidance literature:

With dmap; In dichloromethane; at 0 - 30 ℃; for 3h; Inert atmosphere;

Reference yield: 76.0%

benzyl 2-methyl-3-oxobutanoate (123325-64-4,37526-93-5) → (S)-2-acetoxypropionic acid benzyl ester (151838-56-1)

Guidance literature:

With phenylacetone monooxygenase from Thermobifida fusca; glucose-6-phosphate dehydrogenase; glucose-6-phosphate; NADPH; In dimethyl sulfoxide; at 30 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1002/anie.201103348

Reference yield:

benzyl (S)-Lactate (56777-24-3) + acetyl chloride (75-36-5) → (S)-2-acetoxypropionic acid benzyl ester (151838-56-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;

upstream raw materials:

benzyl (S)-Lactate

acetyl chloride

benzyl bromide

benzyl 2-methyl-3-oxobutanoate

Downstream raw materials:

(S)-2-acetoxypropionic acid

Refernces

• 1、 Hongen, Takahiro,Taniguchi, Tohru,Monde, Kenji. "Modifying oligoalanine conformation by replacement of amide to ester linkage". supporting information. p. 396 - 401. Retrieved 2018/02/13.
• 2、 Rioz-Martínez, Ana,Cuetos, Aníbal,Rodríguez, Cristina,De Gonzalo, Gonzalo,Lavandera, Iván,Fraaije, Marco W.,Gotor, Vicente. "Dynamic kinetic resolution of α-substituted β-ketoesters catalyzed by Baeyer-Villiger monooxygenases: Access to enantiopure α-hydroxy esters". supporting information; experimental part. p. 8387 - 8390. Retrieved 2011/10/09.