305791-05-3

Basic information

• Product Name: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• Synonyms: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS NO: 305791-05-3
• Molecular Weight: 1097.98
• Mol File: 305791-05-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside(305791-05-3)
• EPA Substance Registry System: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside(305791-05-3)

Safety Data

• Hazardous Substances Data: 305791-05-3(Hazardous Substances Data)

Upstream product

• 305791-01-9 1-O-((2S,3S)-2-dimethyl(pentadecen-2-yl)siloxy-3-methoxymethoxy-4-penten-1-yl) 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 305790-95-8 1-O-((2S,3S)-2-hydroxy-3-methoxymethoxy-4-penten-1-yl) 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 305790-89-0 1-O-allyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 305790-94-7 2-oxoethyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 305791-00-8 chloro(dimethyl)(1-pentadecen-2-yl)silane 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 152757-55-6 2-bromo-1-pentadecene 
• 765-13-9 pentadec-1-yne 
• 2595-07-5 allyl β-D-glucopyranoside 
• 591-51-5 phenyllithium 
• 305791-03-1 ((5S,6S)-2,2-dimethyl-5-methoxymethoxy-3-tridecyl-5,6-dihydro-2H-1,2-oxasilin-6-yl)methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 

Downstream Products

• 305791-07-5 (+)-1-O-[(2R,3S,4Z)-2-azido-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 

Relevant articles and documents

Asymmetric allylboration and ring closing alkene metathesis: A novel strategy for the synthesis of glycosphingolipids

A novel strategy for the synthesis of D,L-glucosylceramide 1, a member of the glycosphingolipid class of natural products is described. Reagent-controlled asymmetric Brown allylboration gave excellent stereochemical control in the construction of adjacent stereocenters in the sphingoid base portion of the molecule. The trans-configured double bond was obtained as a single geometrical isomer by use of silicon-tethered olefin metathesis employing the Schrock carbene [(CF3)2MeCO]2Mo-(= CHCMe2Ph)(= NC6H3-2,6-i-Pr2) and in situ PhLi-induced ring-opening of the intermediate 5,6-dihydro-2H-1,2-oxasiline followed by protodesilylation with TBAF in DMSO. The synthesis was completed by long chain amide formation and global deprotection.