321142-09-0

Basic information

• Product Name: methyl 2,3,4,7-tetra-O-benzyl-L-glycero-β-D-allo-heptopyranoside
• Synonyms: methyl 2,3,4,7-tetra-O-benzyl-L-glycero-β-D-allo-heptopyranoside
• CAS NO: 321142-09-0
• Molecular Weight: 584.709
• Mol File: 321142-09-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4,7-tetra-O-benzyl-L-glycero-β-D-allo-heptopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4,7-tetra-O-benzyl-L-glycero-β-D-allo-heptopyranoside(321142-09-0)
• EPA Substance Registry System: methyl 2,3,4,7-tetra-O-benzyl-L-glycero-β-D-allo-heptopyranoside(321142-09-0)

Safety Data

• Hazardous Substances Data: 321142-09-0(Hazardous Substances Data)

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 321142-07-8 methyl 2,3,4-tri-O-benzyl-β-D-allo-hexodialdo-1,5-pyranose 
• 826-19-7 Benzyloxy-methyl-magnesiumchlorid 
• 100-39-0 benzyl bromide 
• 18469-06-2 methyl β-D-allo-pyranoside 
• 305834-12-2 methyl 2,3,4-tri-O-benzyl-β-D-allo-pyranoside 

Relevant articles and documents

Improving the stereoselectivity of one-carbon atom homologation of hexoses at the terminal position

A number of modifications of the original Grignard C1 homologation of hexoses was examined, e.g. reactions of protected hexodialdo-1,5-pyranosides with benzyloxymethyllithium, transmetalation, precomplexation of the aldehydes. Some of the modif

Homologation of protected hexoses with Grignard C1 reagents

Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.