258343-95-2

Basic information

• Product Name: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose
• Synonyms: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose
• CAS NO: 258343-95-2
• Molecular Weight: 522.593
• Mol File: 258343-95-2.mol

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose(258343-95-2)
• EPA Substance Registry System: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose(258343-95-2)

Safety Data

• Hazardous Substances Data: 258343-95-2(Hazardous Substances Data)

Upstream product

• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 14836-50-1 1-[(4S,4S',5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolanyl)-5-yl]ethanone 
• 149880-86-4 (5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-3-(1,2:3,4-di-O-isopropylidene-L-arabino-tetritol-1-yl)-4,5-dihydroisoxazole 

Downstream Products

• 149774-55-0 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-gluco-α-D-gluco-undecofuranose 
• 258280-18-1 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose 

Relevant articles and documents

Aldol reactions on 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose as a route to higher-carbon carbohydrates.

With a view to preparing higher-carbon carbohydrates, crossed-aldol reactions of the methyl ketone 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose with a representative series of aldehydes have been investigated, and the feasibility has been demonstrated o

Aldol reactions on 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose as a route to higher-carbon carbohydrates

With a view to preparing higher-carbon carbohydrates, crossed-aldol reactions of the methyl ketone 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose with a representative series of aldehydes have been investigated, and the feasibility has been demonstrated o

The nitrile oxide-isoxazoline approach to 11-carbon monosaccharides. Conversion of 3-(tetritol-1-yl)-5-(tetrofuranos-4-yl)-2-isoxazolines into 6-deoxyundecoses

Hydrogenolysis of (5R)-3-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-4,5-dihydroisoxazole afforded the 7-ulose derivative, from which 6-deoxy-D-gluco-D-gluco- and D-manno-D-gluco-undecose derivatives 17 and 18 were prepared by reduction with sodium borohydride or L-Selectride. The configuration of the new stereogenic centre (C-7) in compounds 17 and 18 was established by NMR analysis of their 5,7-O-isopropylidene derivatives. 6-Deoxy-L-manno-D-gluco- and L-gluco-D-gluco-undecose analogues 19 and 20 were prepared similarly from the isomeric 3-(L-arabino-tetritolyl)-4,5-dihydroisoxazole. Removal of the isopropylidene protecting groups from compounds 17 and 20 yielded 3-O-benzyl-6-deoxy-D-gluco- and L-manno-D-gluco-undecopyranoses, which were characterised as their octa-acetate derivatives. The corresponding reaction sequence from 3-(D- and L-arabino-tetritol-1-yl)-5-(2,3-O-isopropylidene-3-O-methyl-α-D-lyxo-tetrofuranos-4-yl)-4,5-dihydroisoxazoles afforded 6-deoxy-D/L-gluco-D-manno and D/L-manno-D-manno-undecose derivatives. Copyright (C) 1999 Elsevier Science Ltd.