methyl (2R)-S-tritylthiolactate

Base Information

• Chemical Name: methyl (2R)-S-tritylthiolactate
• CAS No.: 276682-02-1
• Molecular Formula: C₂₃H₂₂O₂S
• Molecular Weight: 362.492
• Mol file: 276682-02-1.mol

Synonyms:methyl (2R)-S-tritylthiolactate

Chemical Property of methyl (2R)-S-tritylthiolactate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R)-S-tritylthiolactate

There total 4 articles about methyl (2R)-S-tritylthiolactate 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: 100.0%

methanol (67-56-1) + (R)-ethyl 2-chloropropanoate (42411-39-2) + triphenylmethanethiol (3695-77-0) → methyl (2R)-S-tritylthiolactate (276682-02-1)

Guidance literature:

With sodium methylate;

DOI:10.1016/S0040-4039(00)00249-5

Reference yield: 48.0%

(R)-ethyl 2-chloropropanoate (42411-39-2) + triphenylmethanethiol (3695-77-0) → methyl (2R)-S-tritylthiolactate (276682-02-1)

Guidance literature:

triphenylmethanethiol; With sodium methylate; In methanol; at 20 ℃; for 1h;

(R)-ethyl 2-chloropropanoate; In methanol; at 20 ℃;

DOI:10.1039/b200921h

Reference yield:

triphenylmethanethiol (3695-77-0) → methyl (2R)-S-tritylthiolactate (276682-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / acetonitrile / 2 h / 20 °C

1.2: 80 percent / acetonitrile / 5 h / 20 °C

2.1: TsOH / 24 h / Heating

With toluene-4-sulfonic acid; triethylamine; In acetonitrile;

DOI:10.1016/S0040-4039(02)02020-8

upstream raw materials:

methanol

(R)-ethyl 2-chloropropanoate

triphenylmethanethiol

Downstream raw materials:

N-propyl-(2S)-S-tritylthiolactamide

S-trityl-2S-thiolactyl-2R-alanine amide

(2S)-S-tritylthiolactic acid

Refernces

• 1、 Harding, Ross L.,Henshaw, Joanne,Tilling, Joannah,Bugg, Timothy D.H.. "Thioester analogues of peptidoglycan fragment MurNAc-L-Ala-γ-D-Glu as substrates for peptidoglycan hydrolase MurNAc-L-Ala amidase". . p. 1714 - 1722. Retrieved 2007/10/03.