851982-09-7

Basic information

• Product Name: (2R,3S,4R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-heptadecan-4-ol
• Synonyms: (2R,3S,4R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-heptadecan-4-ol
• CAS NO: 851982-09-7
• Molecular Weight: 645.054
• Mol File: 851982-09-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-heptadecan-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-heptadecan-4-ol(851982-09-7)
• EPA Substance Registry System: (2R,3S,4R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-heptadecan-4-ol(851982-09-7)

Safety Data

• Hazardous Substances Data: 851982-09-7(Hazardous Substances Data)

Upstream product

• 851981-56-1 Acetic acid (4R,5R)-5-[(1R,2R)-2-acetoxy-1-((R)-2-benzyloxy-1-methyl-ethyl)-pentadecyl]-2,2-dimethyl-[1,3]dioxolan-4-yl ester 
• 851981-55-0 5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 851981-57-2 5-C-dodecyl-3-C-[(R)-β-(benzyloxy-methyl)-ethyl]-3,5-di-deoxy-D-ribofuranose 
• 851981-53-8 5-C-dodecyl-3-C-[(methoxycarbonyl)methyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-ribofuranose 
• 851982-08-6 (R)-2-((3aR,5R,6R,6aR)-2,2-Dimethyl-5-tridecyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-propan-1-ol 
• 851981-54-9 5-C-dodecyl-3-C-[(R)-α-(methoxycarbonyl)-ethyl]-3,5-di-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 851982-07-5 [(3aR,5R,6R,6aR)-2,2-Dimethyl-5-((E)-tridec-1-enyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid methyl ester 
• 15510-55-1 dodecyltriphenylphosphonium bromide 
• 54208-04-7 dodecylidenetriphenylphosphorane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 851981-58-3 (2R,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methyl-heptadecylbenzyl ether 

Downstream Products

• 851981-59-4 (2R,3R,4S)-4-O-tetrahydropyranyl-3-[(tert-butyl-diphenylsilyloxy)methyl]-2-methyl-heptadecan-1-ol 
• 851981-60-7 (1RS,2R,3R,4S)-1-hydroxy-2-methyl-3-[(tert-butyldiphenylsilyloxy)methyl]-4-tridecyl-tetrahydrofuran 
• 851981-61-8 (3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-5-tridecyl-dihydro-furan-2-one 
• 851982-10-0 [(2S,3R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-3-(tetrahydro-pyran-2-yloxy)-hexadecyloxy]-tert-butyl-diphenyl-silane 

Relevant articles and documents

Facially controlled C-methylation of oxolanyl and cyclopentyl acetate enolates: Application to the total synthesis of (+)-nephromopsinic acid

The stereoselectivity of the C-methylation of oxolanyl and cyclopentyl acetate enolates 5a-22a was investigated. The configuration of the C-methyl diastereomers was elucidated by a combination of crystal structure analysis, NMR spectroscopy and chemical correlations. Generally, the methylation proceeded re*-selectively, although with very different degrees of selectivity. The most important stereodirecting effect was a steric one exerted by the 5-phenethyl substituent, and this steric effect was strongly increased by the stereodirecting effect of a 3-OR group. Contrary to previous literature evidence, the endocyclic oxolanyl oxygen does not exert an effect. These findings were applied in a highly stereoselective synthesis of (+)-nephromopsinic acid (94). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.