70491-75-7

Basic information

• Product Name: methyl (S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate
• CAS NO: 70491-75-7
• Molecular Weight: 175.252
• Mol File: 70491-75-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate(70491-75-7)
• EPA Substance Registry System: methyl (S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate(70491-75-7)

Safety Data

• Hazardous Substances Data: 70491-75-7(Hazardous Substances Data)

Upstream product

• 85929-61-9 methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 

Relevant articles and documents

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.