137600-27-2

Basic information

• Product Name: methyl 2-deoxy-2-C-(hydroxymethyl)-β-D-arabino-pentofuranoside tri-O-benzoate
• CAS NO: 137600-27-2
• Molecular Weight: 490.51
• Mol File: 137600-27-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 2-deoxy-2-C-(hydroxymethyl)-β-D-arabino-pentofuranoside tri-O-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-deoxy-2-C-(hydroxymethyl)-β-D-arabino-pentofuranoside tri-O-benzoate(137600-27-2)
• EPA Substance Registry System: methyl 2-deoxy-2-C-(hydroxymethyl)-β-D-arabino-pentofuranoside tri-O-benzoate(137600-27-2)

Safety Data

• Hazardous Substances Data: 137600-27-2(Hazardous Substances Data)

Upstream product

• 23600-19-3 methyl 3-O-tosyl-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 

Relevant articles and documents

Lithium aluminium hydride reduction of glycopyranoside-monosulfonates: Formation of branched furanosides

Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions: (1) stereospecific 1,2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O: for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-α-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.