155195-20-3

Basic information

• Product Name: Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-β-D-galactopyranoside
• CAS NO: 155195-20-3
• Molecular Weight: 1071.31
• Mol File: 155195-20-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-β-D-galactopyranoside(155195-20-3)
• EPA Substance Registry System: Benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->6)-2,3-di-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-β-D-galactopyranoside(155195-20-3)

Safety Data

• Hazardous Substances Data: 155195-20-3(Hazardous Substances Data)

Upstream product

• 4304-12-5 benzyl β-D-galactopyranoside 
• 155194-93-7 Benzoic acid (2R,3R,4R,4aS,10aR)-2-benzyloxy-3-hydroxy-6,6,8,8-tetraisopropyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocycloocten-4-yl ester 
• 155194-92-6 benzyl 3-O-benzoyl-β-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 155194-94-8 Benzyl 2,3-di-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-β-D-galactopyranoside 

Relevant articles and documents

REGIOSELECTIVE GLYCODESILYLATION OF SILYLATED GLYCOSIDES AS A USEFUL TOOL FOR THE PREPARATION OF OLIGOSACCHARIDES

A series of fully or partially protected alkyl and aryl 4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-D-glucopyranosides and 1-thio-β-D-glucopyranosides, respectively, were glycosylated by acetylated α-D-glucopyranosyl-, galactopyranosyl- and cellobiosyl fluoride under Lewis acid-catalysis to give the corresponding β-(1->6)-linked di- and trisaccharides, respectively, in moderate to high yield.With benzylated glucopyranosyl fluoride, anomeric mixtures of disaccharides were obtained depending on the solvent that was used for the glycosylation step.The initially formed oligosaccharides having a 1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl substituent at position 4 were converted by treatment with tetrabutylammonium fluoride into the corresponding 4-OH compounds which are suitable as glycosyl acceptors for further extension of the sugar chain.Selective glycodesilylation of methyl 2-O-benzoyl-6-O-dimethylthexylsilyl-3,4-O-(1,1,3,3,-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-glucopyranoside at position 6 without affecting positions 3 and 4 was possible under similar conditions. 4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxsane-1,3-diyl)-protected D-glycopyranosyl donors (fluoride, chloride, trichloroacetimidate and ethyl 1-thio-glycoside) of glucose and mannose were also prepared and used for the construction of the corresponding silylated disaccharides.Regioselective ring opening of the silylated glycosides by pyridine-polyhydrogen fluoride gave useful glycosyl acceptors that were subsequently coupled with 2,3,4,6-tetra-O-acetyl-α D-glucopyranosyl trichloroacetimidate.