6207-44-9

Basic information

• Product Name: 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran
• CAS NO: 6207-44-9
• Molecular Weight: 580.721
• Mol File: 6207-44-9.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran(6207-44-9)
• EPA Substance Registry System: 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran(6207-44-9)

Safety Data

• Hazardous Substances Data: 6207-44-9(Hazardous Substances Data)

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 100-44-7 benzyl chloride 
• 48149-74-2 allyl D-glucopyranoside 
• 63053-84-9 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 214333-67-2 (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)methylene acetate 
• 1469-70-1 allyl ethyl carbonate 
• 194088-19-2 (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 173206-22-9 Eth-2-al-1-yl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 168253-07-4 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran 
• 141196-28-3 trimethyl(((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)ethynyl)silane 
• 168105-48-4 C₇₂H₇₀O₁₀ 
• 1384643-96-2 C₄₅H₄₄N₂O₆ 
• 1384643-91-7 C₄₃H₄₃NO₆ 
• 1384643-90-6 C₄₃H₄₃NO₆ 
• 1384643-88-2 C₄₃H₄₁NO₈ 
• 1384643-86-0 C₄₄H₄₁NO₉ 
• 168336-52-5 C₃₉H₄₄O₆Si 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Relevant articles and documents

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions

Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of

Glycosyl ortho-Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

We describe the β-ortho-methoxybenzoate as a shelf stable and practical C-1 nucleofuge for catalytic chemical glycosylation in which the benzoic acid by-product can be easily removed, reisolated, and potentially recycled after the glycosylation reaction. This new type of glycosyl donor can be efficiently activated by a range of promoters, including Bi(OTf)3, Fe(OTf)3, TMSOTf (TMS = trimethylsilyl), and triflic acid, with low (10 mol-%) catalyst loadings. The donor shows higher reactivity than analogous benzoate, p-methoxybenzoate and p-cyano-o-methoxybenzoate donors. In glycosylation reactions with o-methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate-based secondary alcohol. Furthermore, β-selective mannosylation was achieved with a Crich-type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first step of a one-pot two-step glycosylation to obtain a trisaccharide; the second coupling involved activation of a thioglycoside with NIS/TMSOTf (NIS = N-iodosuccinimide). We believe that this offers a good alternative to current protocols.