116490-93-8

Basic information

• Product Name: (E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester
• CAS NO: 116490-93-8
• Molecular Weight: 250.295
• Mol File: 116490-93-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester(116490-93-8)
• EPA Substance Registry System: (E)-(4S)-4-benzyloxymethoxypent-2-enoic acid methyl ester(116490-93-8)

Safety Data

• Hazardous Substances Data: 116490-93-8(Hazardous Substances Data)

Upstream product

• 63296-55-9 (S)-(-) ethyl 2-<(benzyloxy)ymethoxy>propanoate 
• 3587-60-8 Benzyloxymethyl chloride 
• 63296-56-0 (S)-(benzyloxymethoxy)propanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 

Downstream Products

• 116490-96-1 (2R,3R,4S)-4-Benzyloxymethoxy-2,3-dihydroxy-pentanoic acid methyl ester 
• 116491-21-5 (2S,3S,4S)-4-Benzyloxymethoxy-2,3-dihydroxy-pentanoic acid methyl ester 
• 116491-06-6 (2S)-(3R)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyxylonic acid methyl ester 
• 116525-13-4 (2R)-(3S)-(4S)-2,3-O-isopropylidene-4-O-benzyloxymethoxyarabinonic acid methyl ester 
• 116560-94-2 (2S)-(3R)-(4S)-5-deoxyxylono-1,4-lactone 
• 76647-70-6 (3R,4R,5S)-3,4-dihydroxy-5-methyldihydrofuran-2(3H)-one 

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.