Methyl 2-(S)-acetoxy-3-carboxypropanoate

Base Information

• Chemical Name: Methyl 2-(S)-acetoxy-3-carboxypropanoate
• CAS No.: 39701-84-3
• Molecular Formula: C7H10O6
• Molecular Weight: 190.153
• European Community (EC) Number: 630-975-3
• Mol file: 39701-84-3.mol

Synonyms:METHYL 2-(S)-ACETOXY-3-CARBOXYPROPANOATE;39701-84-3;AKOS006286536

Chemical Property of Methyl 2-(S)-acetoxy-3-carboxypropanoate

Chemical Property:

• PSA: 89.90000
• LogP: -0.43420
• Solubility.: Ethyl Acetate, Methanol
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 190.04773803
• Heavy Atom Count: 13
• Complexity: 221

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-(S)-Acetoxy-3-carboxypropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(CC(=O)O)C(=O)OC
• Isomeric SMILES: CC(=O)O[C@@H](CC(=O)O)C(=O)OC
• Uses: Methyl 2-(S)-Acetoxy-3-carboxypropanoate (cas# 39701-84-3) is a compound useful in organic synthesis.

Technology Process of Methyl 2-(S)-acetoxy-3-carboxypropanoate

There total 2 articles about Methyl 2-(S)-acetoxy-3-carboxypropanoate 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:

methanol (67-56-1) + (S)-acetoxysuccinic anhydride (59025-03-5) → (S)-2-Acetoxy-succinic acid 1-methyl ester (39701-84-3)

Guidance literature:

Yield given; Ambient temperature;

Reference yield:

methanol (67-56-1) + (S)-Malic acid (97-67-6,78644-42-5) + acetyl chloride (75-36-5) → (S)-2-Acetoxy-succinic acid 1-methyl ester (39701-84-3)

Guidance literature:

Yield given. Multistep reaction; 1.) reflux, 3 h, 2.) 50 deg C, 30 min;

DOI:10.1055/s-1981-29479

Reference yield: 83.0%

(S)-2-Acetoxy-succinic acid 1-methyl ester (39701-84-3) → (3S)-hydroxy-γ-butyrolactone (5469-16-9,58081-05-3,131432-37-6,7331-52-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; tert-butyl alcohol; for 2h; Heating;

upstream raw materials:

methanol

(S)-Malic acid

acetyl chloride

(S)-acetoxysuccinic anhydride

Downstream raw materials:

(3S)-hydroxy-γ-butyrolactone

(S)-2-Acetoxy-heptanoic acid methyl ester

(2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropanamido)-3-t-butoxycarbonylpropanoyl]azetidine-2-carboxylic acid t-butyl ester

methyl (S)-2-hydroxy-4-oxo-5-phenylpentanoate