(-)-methyl (R)-2-thioxothiazolidine-4-carboxylate

Base Information

• Chemical Name: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate
• CAS No.: 80963-80-0
• Molecular Formula: C5H7NO2S2
• Molecular Weight: 177.24500
• Mol file: 80963-80-0.mol

Synonyms:(4R)-methoxycarbonyl-1,3-thiazolidine-2-thione;4(R)-(methoxycarbonyl)thiazolidine-2-thione;(R)-methyl-2-thioxothiazolidine-4-carboxylate;4(R)-methoxycarbonyl-1,3-thiazolidine-2-thione;methyl (R)-2-thioxothiazolidine-4-carboxylate;4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione;(R)-2-Thioxo-thiazolidine-4-carboxylic acid methyl ester;

Chemical Property of (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate

Chemical Property:

• PSA: 95.72000
• LogP: 0.47810

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate

There total 4 articles about (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate 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: 99.0%

methanol (67-56-1) + (4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid (98169-56-3) → 4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione (80963-80-0)

Guidance literature:

With titanium tetrachloride; at 20 ℃; for 12h; chemoselective reaction;

DOI:10.1016/j.tet.2014.01.006

Reference yield: 93.7%

(R)-3-Hexadecanoyl-2-thioxo-thiazolidine-4-carboxylic acid methyl ester (81912-43-8) + phenylglycine methyl ester (24461-61-8,26682-99-5,37760-98-8,6591-61-3) → 4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione (80963-80-0) + (S)-Hexadecanoylamino-phenyl-acetic acid methyl ester (81912-46-1)

Guidance literature:

In dichloromethane; for 12h; Product distribution; Ambient temperature; Asymmetric amidation of racemic amines by optically active acylthiazolidines. E_.e. of products 0.2-64.4percent; solvent effect.;

DOI:10.1016/S0040-4039(00)86785-4

Reference yield: 87.1%

carbon disulfide (75-15-0,12122-00-8) + L-cysteine methyl ester hydrochloride (18598-63-5) → 4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione (80963-80-0)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00387a016

upstream raw materials:

carbon disulfide

L-cysteine methyl ester hydrochloride

1,1'-Thiocarbonyldiimidazole

(R)-3-Hexadecanoyl-2-thioxo-thiazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

C₂₀H₂₄N₂O₆S₄

(4S,5S)-4-Cyclohexylmethyl-5-[(1R,2R)-1-hydroxy-2-((R)-4-methoxycarbonyl-2-thioxo-thiazolidine-3-carbonyl)-3-methyl-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

3-(3(R)-(3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-3-hydroxy-2(R)-isopropyl-1-oxopropyl)-4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione

methyl 3-benzoyl-2-thioxothiazolidine-4-carboxylate

Refernces

• 1、 Lai, Qi,Li, Yang,Gong, Zhiyong,Liu, Qingwen,Wei, Chiyu,Song, Zhiguang. "Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions". . p. 979 - 988. Retrieved 2015/11/16.
• 2、 Chen, Ning,Jia, Weiyi,Xu, Jiaxi. "A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines". supporting information; experimental part. p. 5841 - 5846. Retrieved 2010/03/03.