88819-23-2

Upstream product

• 100-39-0 benzyl bromide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 100-44-7 benzyl chloride 
• 40010-11-5 methyl α-D-galactopyranoside 3-benzyl ether 

Downstream Products

• 1454799-53-1 O-ethyl-S-[(((methyl 3,6-di-O-benzyl-α-D-galactopyranos-2-yl)dimethylsilyl)methyl)]dithiocarbonate 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 81086-90-0 methyl 3,4,6-tri-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates

A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl

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.

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.