155205-42-8

Basic information

• Product Name: methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside
• Synonyms: methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside
• CAS NO: 155205-42-8
• Molecular Weight: 446.616
• Mol File: 155205-42-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside(155205-42-8)
• EPA Substance Registry System: methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside(155205-42-8)

Safety Data

• Hazardous Substances Data: 155205-42-8(Hazardous Substances Data)

Upstream product

• 40653-21-2 methyl 2,3,4,7-tetra-O-acetyl-6-deoxy-α-D-manno-heptopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 155205-44-0 methyl 6-deoxy-2,3-O-isopropylidene-7-O-tert-butyldiphenylsilyl-α-D-talo-heptopyranoside 
• 155205-43-9 methyl 6-deoxy-2,3-O-isopropylidene-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside 

Relevant articles and documents

Syntheses of methyl glycosides of 6-deoxyheptoses

Methyl α-D-glycopyranosides of 6-deoxy-D-altro-heptose, 6-deoxy-D-manno-heptose, and 6-deoxy-D-talo-heptose have been prepared. Displacements of methyl 2,3,4-tri-O-benzylhexopyranoside 6-trifluoromethanesulfonates with potassium cyanide, followed by reduction of the resulting heptopyranosidurononitriles with diisobutylaluminum hydride, hydrolysis of the imine, further reduction with sodium borohydride, and catalytic O-debenzylation, give the corresponding methyl 6-deoxyheptopyranosides. Configurational change at C-4 of methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside to give the talo isomer was effected by oxidation followed by stereoselective reduction. 1H nuclear magnetic resonance data of the glycosides, and gas chromatography of acetylated glycosides of (R)- and (S)-2-butanol serve to establish ring and enantiomeric configurations of the parent sugars when these are encountered as constituents of lipopolysaccharides or extracellular carbohydrate polymers, as in Campylobacter species.