58781-26-3

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 80-97-7 Cholestanol 
• 77988-16-0 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-6)-2,4-di-O-benzyl-α-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 139608-10-9 methyl 2,3,6-tri-O-benzyl-4-O-isopropenyl-α-D-glucopyranoside 
• 108-93-0 cyclohexanol 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 872123-62-1 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 60-12-8 2-phenylethanol 
• 1370590-24-1 2-allylphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 1370590-22-9 2-allylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 83-87-4 D-Mannose pentaacetate 
• 100-39-0 benzyl bromide 

Downstream Products

• 99-20-7 TREHALOSE 
• 827026-13-1 6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose 
• 827026-14-2 (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester 
• 827026-12-0 6-azido-2,2',3,3',4,4',6'-hepta-O-benzyl-6-deoxy-α,α'-trehalose 
• 827026-15-3 (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide 
• 1442888-53-0 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1→1)-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 1442888-57-4 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1→1)-6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 103128-35-4 2,3,4,2’,3’,4’,6’-hepta-O-benzyl-α,α’-trehalose 

Relevant academic research and scientific papers

Synthesis of N-Glycosides.Formation of Glucosylamine by Reaction of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose with Acetonitrile in the Presence of Trifluoromethanesulfonic Anhydride

The synthesis of glucosylamine by reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose with acetonitrile in the presence of trifluoromethanesulfonic anhydride was shown to proceed through an intermediate oxazoline.

A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride (NfF)

A new dehydrative glycosylation protocol that proceeds through selective activation of glycosyl hemiacetals with nonafluorobutanesulfonyl fluoride (NfF) has been disclosed. Contrary to the major classical glycosylation reactions that proceed under acidic

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

2-Allylphenyl glycosides as glycosyl donors for sugar coupling

Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins.

Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation

This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1 -hydroxy sugars with some primary alcohols in the presence of on

2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors

A high-yielding coupling of a new and stable type of glycosyl donors, namely 2-allyloxyphenyl glycoside, with a variety of alcohols via NIS/TfOH reagent combination as effective activators at room temperature is described here.

Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation

A versatile glycosylation reaction is used to establish the process of sulfoxide covalent catalysis. Hemiacetals are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, nBu2SO, for coupling with various nucleophiles (Nu; se

Synthesis of methyl O-α-D-mannosyl-(1→4)-[(3-O-methyl-α-D-mannosyl) -(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via dehydrative glycosylation

Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl -(1→4)-]n3-O-methyl-α-D-mannopyra-nosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.

A new, efficient glycosylation method for oligosaccharide synthesis under neutral conditions: Preparation and use of new DISAL donors

Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3,5-dinitrobenzoate (DISAL) and its para regioisomer, methyl 4-hydroxy-3,5-dinitrobenzoate, were prepared by nucleophilic aromatic substitution. In a first demonstration of their potential as glycosyl donors, stereospecific glycosylation of methanol was achieved. In the glycosylation of more hindered alcohols, the β-donor proved more reactive, and α-glucosides were predominantly formed. Glycosylation of protected monosaccharides, with free 6-0H or 3-OH, proceeded smoothly in 1-methyl-2-pyrrolidinone (NMP) at 40-60 °C in the absence of Lewis acids and bases in good to excellent yields. Glycosylation of 3-OH gave the α-linked disaccharide only.

Rational design and synthesis of a 1,1-linked disaccharide that is 5 times as active as sialyl Lewis X in binding to E-selectin

We describe here a rational design and synthesis of (3-O-carboxymethyl)-β-D-galactopyranosyl α-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-g