25019-43-6

Basic information

• Product Name: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>
• Synonyms: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>
• CAS NO: 25019-43-6
• Molecular Weight: 376.428
• Mol File: 25019-43-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>(25019-43-6)
• EPA Substance Registry System: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>(25019-43-6)

Safety Data

• Hazardous Substances Data: 25019-43-6(Hazardous Substances Data)

Upstream product

• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 

Downstream Products

• 1053727-37-9 Toluene-4-sulfonic acid (2S,3S,4S,5R,6S)-3-azido-4,5,6-trimethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 186414-20-0 Phenyl-[(2R,4aR,6S,7R,8S,8aR)-6,7,8-trimethoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-2-yl]-methanone 
• 186414-25-5 (R)-Phenyl-[(2R,4aR,6S,7R,8S,8aR)-6,7,8-trimethoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-2-yl]-methanol 
• 1053630-87-7 Toluene-4-sulfonic acid (2R,3R,4R,5R,6S)-4,5,6-trimethoxy-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester 

Relevant articles and documents

Synthesis of monosaccharide-fused azetidines

Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by 1H and 13C NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments.

Unprecedented Influence of Azides and the Effect of Bulky Groups on Zinc-induced Reductions of Deoxy Halogeno Sugars

Zinc/silver-graphite induced ring-opening reactions of deoxy halogeno sugars by dealkoxyhalogenation may be suppressed by bulky protecting goups in the substrates, giving rise to simple dehalogenation products.Furanose derivatives are more sensitive to such steric effects than pyranose systems, although an X-ray analysis of 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-5-iodo-α-D-xylofuranose 3 shows no evidence of steric hindrance by the C-3 substituent.Morever, dehalogenation instead of reductive ring-opening reactions are observed in all cases in which organic azides are present in the reaction medium.This unprecedented effect of azides on zinc-induced reductions is equally effective both intra- and intermolecularly.This behaviour is best rationalized by assuming radical intermediates for dehalogenations, in contrast to transient organometallic species closely bound to the zinc surface when reductive ring-opening is observed.This mechanistic interpretation is supported by a labelling experiment.