449729-39-9

Upstream product

• 157020-34-3 (2R,4R)-4-formyl-2-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 161458-78-2 (2R,4R)-4-(hydroxymethyl)-2-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 449729-37-7 (2R,4R)-4-((S)-Cyano-trimethylsilanyloxy-methyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 452100-77-5 (2R,4R)-4-(Cyano-trimethylsilanyloxy-methyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 1025879-11-1 (2R,4R)-4-((S)-6-Carboxy-2-oxo-1-trimethylsilanyloxy-hexyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 189228-43-1 (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester 
• 99380-83-3 (2RS,4R)-4-(hydroxymethyl)-2-phenylthiazolidine 
• 100-52-7 benzaldehyde 

Downstream Products

• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 449729-46-8 5-[(3S,4R)-4-(1-Benzyl-ureido)-3-methoxycarbonyloxy-dihydro-thiophen-(2E)-ylidene]-pentanoic acid methyl ester 
• 608-16-2 biotin methyl ester 
• 58-85-5 biotin 
• 449729-48-0 5-[(3aS,6aR)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(4Z)-ylidene]-pentanoic acid methyl ester 

Relevant academic research and scientific papers

A highly stereocontrolled total synthesis of (+)-biotin from L-cysteine

(+)-Biotin was synthesized in 11 steps and in 25% overall yield from readily accessible L-cysteine through a Lewis base-catalyzed highly diastereoselective cyanosilylation of (2R,4R)-N-Boc-2-phenylthiazolidine-4-carbaldehyde 2 and a ring closure of a cis-allylic carbonate 5b utilizing a palladium-catalyzed intramolecular allylic amination.

A novel synthesis of (+)-biotin from L-cysteine

(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.