374751-42-5

Basic information

• Product Name: ba-L-Mannopyranose, 1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy- (9CI)
• Synonyms: bta-L-Mannopyranose,1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy-(9CI);ba-L-Mannopyranose, 1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy- (9CI)
• CAS NO: 374751-42-5
• Molecular Formula: C9H13NO5
• Molecular Weight: 215.20322
• Product Categories: ALCOHOL
• Mol File: 374751-42-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ba-L-Mannopyranose, 1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: ba-L-Mannopyranose, 1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy- (9CI)(374751-42-5)
• EPA Substance Registry System: ba-L-Mannopyranose, 1,2-O-[(1R)-1-cyanoethylidene]-6-deoxy- (9CI)(374751-42-5)

Safety Data

• Hazardous Substances Data: 374751-42-5(Hazardous Substances Data)

Upstream product

• 76250-05-0 3,4-di-O-acetyl-1,2-exo-cyanoethylidene-β-L-rhamnose 
• 69908-87-8 3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-6-deoxy-α-D-glucopyranose 
• 69908-87-8 3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-rhamnopyranose 
• 155485-69-1 3,4-Di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-fucopyranose 
• 4026-27-1 1,2:3,4-di-O-isopropylidene-α-D-fucopyranose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 
• 5158-64-5 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 

Downstream Products

• 76235-18-2 4-O-acetyl-3-O-trityl-1,2-exo-cyanoethylidene-L-rhamnopyranose 

Relevant articles and documents

SYNTHESIS OF POLYSACCHARIDE Α-(1-3)-L-RHAMNAN

The regular polysaccharide α-(1-3)-L-rhamnan (DP ca. 30) was obtained by polycondensation of 4-O-acetyl-3-O-trityl-1,2-O-exo-cyanoethylidene-L-rhamnopyranose catalysed with triphenylmethylium perchlorate.

SYNTHESIS AND POLYCONDENSATION OF GALACTO-CONFIGURATED MONOMERS VIA THE TRITYL-CYANO-ETHYLIDENE-PROCEDURE

4-O-Acetyl-1,2--3-O-trityl-α-D-fucopyranose (13) and methyl 4-O-acetyl-1,2-O--3-O-trityl-α-D-galactopyranuronate (14) were synthesised.Trityl-cyanoethylidene condensation of the monomer 14 gave protected β-D-GalpA-(1->3)-D-GalpA-oligosaccharide derivatives with high stereoselectivity and a degree of polymerisation (d.p.) of eight.In the case of the D-fucose monomer 13, the yield of oligomers is surprisingly low and the d.p. does not exceed seven.This result is in contrast to the d.p. 20 - 60 obtained with other 6-deoxy-sugars, as previously described by Kochetkov and coworkers.

THE EFFECT OF HIGH PRESSURE ON THE STEREOSPECIFICITY OF THE GLYCOSYLATION REACTION

At a pressure of 1,4 GPa and room temperature, the glycosylation of trityl ethers by 1,2-O-cyanoethylidene derivatives of sugars, and the polycondensation of the proper monomers in dichloromethane, proceed with absolute stereospecificity, giving rise to a