556834-62-9

Upstream product

• 130247-99-3 1-[4-benzyl-2-oxo-(4S)-1,3-oxazolidin-3-yl]-2-methyl-3-phenylsulfanyl-(2S)-propan-1-one 
• 121783-49-1 (S)-(+)-2-methyl-3-(phenylthio)propan-1-ol 
• 556834-61-8 methyl 4-methyl-5-phenylsulfinyl-(Z,4S)-2-pentenoate 
• 556834-58-3 methyl 4-methyl-5-phenylsulfanyl-(Z,4S)-2-pentenoate 

Downstream Products

• 556834-69-6 methyl 5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylsulfinyl-(E,5S,6S)-2-heptenoate 
• 556834-67-4 methyl 3-(tert-butyldiphenylsilyloxy)-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate 
• 556834-68-5 (3S,4S)-5-Benzenesulfinyl-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-pentanal 
• 186193-13-5 methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate 
• 218269-05-7 methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate 
• 556834-64-1 (2R,3R,4S)-5-Benzenesulfonyl-2-bromo-4-methyl-pentane-1,3-diol 
• 556834-66-3 methyl 3-hydroxy-4-methyl-5-phenylsulfinyl-(3S,4S)-pentanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines

A stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucine is disclosed. The key step of the reaction sequence involves, stereo- and regioselective bromohydration of 7, using a brominating agent derived in situ from N-bromosuccinimide and 2,6-lutidine, via intramolecular sulfinyl group participation.

Sulfinyl moiety as an internal nucleophile. 1. Efficient stereoselective synthesis of fragment A of cryptophycin 3

A novel, efficient, and stereoselective synthesis of fragment A of cryptophycin 3 is disclosed. The key step involves the regio- and stereoselective transformation of an unsaturated ester to a bromohydrin via anchimeric assistance by the sulfinyl group.