53685-11-3

Upstream product

• 102854-30-8 methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 127563-77-3 methyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 35526-05-7 6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 23392-30-5 methyl 6-O-benzyl-α-D-galactopyranoside 
• 40269-01-0 methyl 3,4-O-isopropylidene-α-D-galactopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 1454799-48-4 O-ethyl-S-[(((methyl 2,3,6-tri-O-benzyl-α-D-galactopyranos-4-yl)dimethylsilyl)methyl)]dithiocarbonate 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 59-23-4 D-Galactose 

Downstream Products

• 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 
• 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 
• 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 
• 934592-21-9 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 7115-19-7 methyl β-D-galactopyranosyl-<1->3>-β-D-galactopyranoside 
• 102854-35-3 Methyl-2,6-di-O-benzyl-3-O-β-D-galactopyranosyl-β-D-galactopyranosid 
• 1173284-93-9 methyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-5-N-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 1227468-52-1 methyl [methyl (4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 136737-07-0 methyl 4,5,7,8,9-penta-O-acetyl-2,3,5-trideoxy-D-glycero-D-galacto-non-2-eno-pyranosonate 

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

A tin-free regioselective radical de-o-benzylation by an intramolecular hydrogen atom transfer on carbohydrate templates

Radically selective: A remarkable 1,7-hydrogen atom transfer of a benzylic hydrogen atom to an O-silylmethylene radical initiates a regioselective de-O-benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups. Copyright

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

Regiospecific synthesis of 4-deoxy-D-threo-hex-3-enopyranosides by simultaneous activation-elimination of the talopyranoside axial 4-OH with the NaH/Im2SO2 system: Manifestation of the stereoelectronic effect

A new and high-yielding method for the regioselective preparation of 4-deoxy- and 2,4-dideoxy-2-acetamido-β-D-threo-hex-3-enopyranosides has been developed. The process involves a simultaneous activation-elimination of the OH-4 group of β-D-talopyranoside

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.

Synthesis and biological activities of methyl oligobiosaminide and some deoxy isomers thereof.

Methyl oligobiosaminide (1) the core structure of oligostatin C, and five analogues, the 6-hydroxy-(2), 2-deoxy- (3), 2-deoxy-6-hydroxy- (4), 3-deoxy- (5), and 3-deoxy-6-hydroxy derivatives (6), were synthesized by coupling the protected pseudo-sugar epoxide 46 with suitable methyl 4-amino-4-deoxy-alpha-D-hexopyranoside derivatives. Compounds 3 and 6 showed notable inhibitory activity against alpha-D-glucosidase and alpha-D-mannosidase, respectively, whereas compound 1 had almost no activity.