124813-78-1

Basic information

• Product Name: methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
• Synonyms: methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
• CAS NO: 124813-78-1
• Molecular Weight: 596.72
• Mol File: 124813-78-1.mol

Chemical Properties

• CAS DataBase Reference: methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate(124813-78-1)
• EPA Substance Registry System: methyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate(124813-78-1)

Safety Data

• Hazardous Substances Data: 124813-78-1(Hazardous Substances Data)

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 5927-18-4 trimethyl phosphonoacetate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 96-32-2 bromoacetic acid methyl ester 
• 140230-23-5 (E)-methyl 4,5,6,8-tetra-O-benzyl-2,3-dideoxy-D-gluco-oct-2-enonate 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 1193390-74-7 methyl 2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate 
• 493018-20-5 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2-deoxy-D-gluco-oct-2-enonic acid methyl ester 
• 400888-42-8 methyl (2,3,4,6-tetra-O-benzyl-1-hydroxy-D-glucopyranosyl)acetate 
• 114192-64-2 methyl 2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetate 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 81972-20-5 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol 

Relevant articles and documents

A Mitsunobu route to C-glycosides

C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach

C-Glycosylidene derivatives (exo-glycals): Their synthesis by reaction of protected sugar lactones with tributylphosphonium ylids, conformational analysis and stereoselective reduction

Stabilised tributylphosphonium ylids Bu3PCH = CH(EWG), where EWG is CO2Me, CO2tBu or CN, react with protected sugar lactones under mild conditions to give high yields of glycosylidene derivatives (4 and 5) with good Z/E selectivity. X-Ray crystallography shows that in the solid state the tetra-O-benzyl protected (Z)-glucosylideneacetonitrile (Z)-4c adopts a conformation intermediate between a boat and a twist-boat, whereas the isomeric galactose derivative (Z)-5c exists as a distorted chair. NMR data suggest that in solution chair-like conformations are again more favoured for galactosylidene derivatives than for their glucosylidene analogues. Solution phase NMR studies and molecular modelling show that the (E)-double bond geometry disfavours the chair-like geometry of the ring, even in the galactose series; this is consistent with the avoidance of allylic 1,3-strain. Reduction of the glycosylidene double bond to give stereoselective formation of β-C-glycoside derivatives may be achieved by using Et3SiH-CF3CO2H or Et 3SiH-BF3·Et2O.

A new Co(0) complex mediated synthesis of C-glycoside analogues

Properly protected glyconolactones, readily available from the parent sugars, react under mild conditions with α-bromoacetates in the presence of a soluble Co(0) complex, either in stoichiometric or substoichiometric amounts, to give a Reformatsky-type addition product to the lactone. The addition product can be subsequently converted into a variety of compounds: dehydroxylation with triethylsilane in the presence of boron trifluoride affords C-glycosides.

β-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals

Several examples of β-selective C-glycosidation reactions, involving TMSOTf-promoted addition of sterically hindered silyl ketene acetals to glucosyl and galactosyl acetates, are presented.

Synthesis of C-glycosides: Utilizations of a arsenic derivative

Reaction of arsenic ylides with pyranose and furanose carbohydrates mainly leads to E-olefinic derivatives. Cyclisation of the olefinic derivatives obtained from 2,3,4,6-tetra-O-benzyl-D-glucose and D-galactose, promoted by ZnBr2, gives C-glyco

Epimerization of α- to β-C-Glucopyranosides under Mild Basic Conditions

A number of β-C-glucopyranosides having an activated methylene or methine group bonded to the anomeric carbon are obtainable in quantitative yield from the corresponding α-isomers by simple equilibration catalysed by various bases at room temperature.

The Wittig-Horner Reaction on 2,3,4,6-Tetra-O-benzyl-D-mannopyranose and 2,3,4,6-Tetra-O-benzyl-D-glucopyranose

The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α- and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose.A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.