906535-21-5

Basic information

• Product Name: (E)-(4S)-4-benzyloxymethoxy-4-phenylbut-2-enoic acid tert-butyl ester
• CAS NO: 906535-21-5
• Molecular Weight: 354.446
• Mol File: 906535-21-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-(4S)-4-benzyloxymethoxy-4-phenylbut-2-enoic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(4S)-4-benzyloxymethoxy-4-phenylbut-2-enoic acid tert-butyl ester(906535-21-5)
• EPA Substance Registry System: (E)-(4S)-4-benzyloxymethoxy-4-phenylbut-2-enoic acid tert-butyl ester(906535-21-5)

Safety Data

• Hazardous Substances Data: 906535-21-5(Hazardous Substances Data)

Upstream product

• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 906535-18-0 (R)-2-Benzyloxymethoxy-2-phenyl-ethanol 
• 611-71-2 (R)-Mandelic Acid 
• 20698-91-3 (R)-methyl mandelate 
• 171032-44-3 (R)-Benzyloxymethoxy-phenyl-acetic acid methyl ester 

Relevant articles and documents

Iterative synthesis of deoxypropionate units: The inductor effect in acyclic conformation design

Conjugate addition of lithium dimethylcuprate to acyclic α,β-unsaturated esters of varying lengths bearing terminal alkyl or phenyl groups leads to a preponderance of syn 1,3-adducts when one methyl is already present. Conversion to enoates, and iteration of cuprate additions also favors syn adducts to give contiguous deoxypropionate units in a growing chain. The effect of end-group variation (Me, i-Pr, phenyl, tert-butyl) in conjunction with the nature of the ester group (Me, tert-butyl, etc.) on the diastereoselectivity of syn and anti products was studied. The results are rationalized in terms of inductor effects related to the minimization of the 1,5-pentane interactions in energetically favored folded conformations and corroborated by homodecoupling NMR studies.