156327-32-1

Basic information

• Product Name: (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate
• Synonyms: (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate
• CAS NO: 156327-32-1
• Molecular Weight: 248.322
• Mol File: 156327-32-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate(156327-32-1)
• EPA Substance Registry System: (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate(156327-32-1)

Safety Data

• Hazardous Substances Data: 156327-32-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 132836-59-0 (1R,5S,3Z)-5-benzyloxy-1-phenylhex-3-en-1-ol 
• 132836-85-2 (1R,5S,3Z)-1-acetoxy-5-benzyloxy-1-phenyl-3-hexene 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 94233-71-3 (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Effective 1,5-asymmetric induction in tin(IV) chloride promoted reactions between aldehydes and (4-alkoxy-2-alkenyl)tributylstannanes

Transmetallation of (S)-4-benzyloxy-2-pentenyl(tributyl)stannane (1) using tin(IV) chloride generates an allyltin trichloride which reacts in situ with aldehydes to give 1-substituted syn-(3Z)-5-benzyloxyhexenols with excellent stereoselectivity. With chiral aldehydes, the stereoselectivity of the reaction is dominated by the reagent, except for 2-alkoxyaldehydes which show matching and mismatching consistent with preferred Felkin-Anh diastereofacial selectivity.