1027964-53-9

Basic information

• Product Name: (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester
• Synonyms: (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester
• CAS NO: 1027964-53-9
• Molecular Weight: 320.429
• Mol File: 1027964-53-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester(1027964-53-9)
• EPA Substance Registry System: (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid methyl ester(1027964-53-9)

Safety Data

• Hazardous Substances Data: 1027964-53-9(Hazardous Substances Data)

Upstream product

• 906534-76-7 (3S,4R)-4-Benzyloxymethoxy-3,5-dimethyl-hexanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 381246-76-0 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexanoic acid methyl ester 
• 381246-75-9 (E)-(4R)-4-benzyloxymethoxy-5-methylhex-2-enoic acid methyl ester 
• 381247-06-9 (R)-2-Benzyloxymethoxy-3-methyl-butan-1-ol 
• 381247-05-8 (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester 
• 906534-74-5 (R)-2-Benzyloxymethoxy-3-methyl-butyraldehyde 
• 90244-32-9 (R)-methyl 2-hydroxy-3-methylbutanoate 
• 3587-60-8 Benzyloxymethyl chloride 
• 906534-75-6 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexan-1-ol 

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.