86342-20-3

Upstream product

• 102854-30-8 methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 100-44-7 benzyl chloride 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 108739-91-9 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2-O-benzoate 
• 127563-77-3 methyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 4148-71-4 methyl endo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 
• 22277-65-2 Methyl mannoside 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 109681-27-8 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yloxy)-3-hydroxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 109681-26-7 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yloxy)-3-hydroxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside 
• 51842-16-1 methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 55697-53-5 methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 102854-31-9 Methyl-2,6-di-O-benzyl-3,4-O-(1-ethoxyethyliden)-β-D-galactopyranosid 
• 111462-60-3 methyl 3,4-di-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 190782-07-1 (2R,3S,4S,5R,6R)-5-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-tetrahydro-pyran-3-ol 
• 127563-77-3 methyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 286860-87-5 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(ethoxysulfonyl)methylidene-D-glucopyranose 
• 223582-39-6 methyl 2,6-di-O-benzyl-3-O-(3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-α-D-gluco-hept-2-ulopyranosyl)-β-D-galactopyranoside 
• 709040-95-9 C₅₆H₇₂N₂O₂₇ 

Relevant academic research and scientific papers

Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors

The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowle

Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study

Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we analyzed the relative

A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa

Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Halide promoted organotin-mediated carbohydrate benzylation: Mechanism and application

In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl β-d-galactoside. It was demonstrated that the

Reductive openings of benzylidene acetals revisited: A mechanistic scheme for regio- and stereoselectivity

Despite the importance of regioselective reductive openings of cyclic acetals, mechanistic details are scarce. In this study 4,6-O-benzylidene acetals were used as model compounds for deciphering the mechanism of regioselective openings using a variety of

REGIOSELECTIVE FORMATION OF DI-O-BENZYL-SUBSTITUTED HEXOPYRANOSIDES VIA STANNYLENE ACETAL INTERMEDIATES

The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated.These reactions occur readily in benzyl bromide at 85 deg C.At reaction times of one to two days, the major products are di-O-benzyl derivatives.In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70percent yields, respectively.The species present in these reactions and the reaction pathway are discussed.

Regioselective Monoalkylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method

Regioselective monoalkylation of some pento- and hexopyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) was examined by using the dibutyltin oxide method without protecting the hydroxyl groups.By this method, alkylation proceeds more or less in the same fashion as reported for acylation (through the formation of cyclic tin intermediates) and selectively activates an equatorial hydroxyl group which has an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary hydroxyl group.However, in some instances the position of activation is different.Various monoalkyl ethers thus prepared were identified by analyses of their carbon-13 nuclear magnetic resonance spectra.Keywords-regioselective monoalkylation; glycopyranoside; dibutyltin oxide; cis-vicinal glycol; benzylation; allylation; methoxymethylation; methylation;13C-NMR

ENTWICKLUNG EINES SYNTHESEBLOCKS DER 3-O-β-D-GALACTOPYRANOSYL-D-GALACTOPYRANOSE

In the presence of trimethylsilyl triflate, 1,2,3,4,6-penta-O-acetyl-β-D-galactopyranose reacted with benzyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside to give benzyl 2,6-di-O-benzyl-3-O-β-D-galactopyranosyl-β-D-galactopyranoside further converted i

Partial Benzylation of Methyl α- and β-D-Galactopyranosides

Partial benzylation of methyl α-D-galactopyranoside with benzyl chloride and LiOH selectively gave the 2,3,6-tribenzyl ether, while that using KOH or RbOH gave the 2,4,6-isomer as the main product.Methyl β-D-galactopyranoside afforded the 3,4,6-tribenzyl ether predominantly, irrespective of the alkali used.