53929-30-9

Basic information

• Product Name: benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside
• CAS NO: 53929-30-9
• Molecular Weight: 540.656
• Mol File: 53929-30-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside(53929-30-9)
• EPA Substance Registry System: benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside(53929-30-9)

Safety Data

• Hazardous Substances Data: 53929-30-9(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1380516-32-4 3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate 
• 604-69-3 β-D-glucose pentaacetate 
• 82703-48-8 3,4,6-tri-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 
• 4258-14-4 3,4,6-tri-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 

Downstream Products

• 185380-50-1 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 

Relevant articles and documents

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Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups

In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.