121534-53-0

Basic information

• Product Name: tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate
• Synonyms: tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate
• CAS NO: 121534-53-0
• Molecular Weight: 296.431
• Mol File: 121534-53-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate(121534-53-0)
• EPA Substance Registry System: tert-butyl (3S,4S)-3-hydroxy-4-(benzyloxy)thiopentanoate(121534-53-0)

Safety Data

• Hazardous Substances Data: 121534-53-0(Hazardous Substances Data)

Upstream product

• 999-90-6 S-tert-butyl thioacetate 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 121534-52-9 1-(tert-butyldimethylsiloxy)-1-(tert-butylsulfanyl)ethene 
• 63584-47-4 (1-tert-butylsulfanyl-vinyloxy)trimethylsilane 

Relevant articles and documents

Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-statine

Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacetate-derived chiral enolates and enantiopure N,N-dibenzyl α-amino aldehydes, either the 3,4- anti or the 3,4-syn aldol adduct can be obtained with very high diastereoselectivity just by changing the chiral boron ligand configuration. The above procedure was used for a stereoselective total synthesis of (3S,4S)-statine.

Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes

Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences.