95189-57-4

Upstream product

• 30608-21-0 2,3,4,6-tetra-O-benzyl-1-O-trimethylsilyl-α,β-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 53270-14-7 benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 77988-17-1 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-6)-2,4-di-O-benzyl-α-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 161442-11-1 2,3,4,6-Tetra-O-benzoyl-α-L-glucopyranosyl bromide 
• 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 
• 60-12-8 2-phenylethanol 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

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.

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

SYNTHESIS OF UNSYMMETRICAL TREHALOSE ANALOGUES BY SILVER TRIFLUOROMETHANESULPHONATE PROMOTED GLYCOSYLATIONS

The coupling of benzoylated glucosyl bromides with 2,3,4,6-tetra-O-benzylated gluco, manno or galacto-pyranoses promoted by silver triflate is described, and the compositions of the crude reaction mixtures, determined by 13C NMR spectroscopy, are presente

The Use of O-Glycosyl Trichloroacetimidates in The Synthesis of Unsymmetrical Trehalose Analogues

The coupling of O-glycosyl trichloroacetimidates with 2,3,4,6-tetra-O-benzylated monosaccharides (gluco, manno, galacto) promoted by TMSOTf is described, and the compositions of the crude reaction mixtures, determined by 13C NMR spectroscopy, are presente

THE HIGHLY STEREOSELECTIVE SYNTHESIS OF PERBENZYLATED α,α-TREHALOSE AND ITS D-GALACTO AND D-MANNO ANALOGS

Treatment of 2,3,4,6-tetra-O-benzyl-1-O-trimethylsilyl-α,β-D-glucopyranose in dichloromethane with trimethylsilyl triflate catalyst gave the corresponding α,α- and α,β-trehaloses in quantitative yield.A similar treatment of D-galacto and D-manno analogs gave exclusively the corresponding α,α-anomers, respectively.

ONE-STAGE GLYCOSYLATION USING PROTECTED GLYCOSE: THE SYNTHESIS OF O-β-D-GLUCOPYRANOSYL-(1->3)-O-6)>-D-GLUCOPYRANOSE

The one-stage β-glycosilation of benzyl 3-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside ( 1 ) with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose ( 2 ) using a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, followed by deacetylation, gave benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,4-di-O-benzyl-α-D-glucopyranoside ( 3 ).The disaccharide derivative 3 was then subjected to the β-glucosylation, followed by catalytic hydrogenation, to afford O-β-D-glucopyranosyl-(1->3)-O-6)>-D-glucopyranose ( 4 ).The key intermediate 1 was prepared from D-glucose by way of a Fischer reaction, triphenylmethylation, a controlled benzylation, and detriphenylmethylation.