67381-30-0

Basic information

• Product Name: methyl 3,6-di-O-benzyl-β-D-galactopyranoside
• Synonyms: methyl 3,6-di-O-benzyl-β-D-galactopyranoside
• CAS NO: 67381-30-0
• Molecular Weight: 374.434
• Mol File: 67381-30-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 3,6-di-O-benzyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3,6-di-O-benzyl-β-D-galactopyranoside(67381-30-0)
• EPA Substance Registry System: methyl 3,6-di-O-benzyl-β-D-galactopyranoside(67381-30-0)

Safety Data

• Hazardous Substances Data: 67381-30-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 100-44-7 benzyl chloride 
• 40010-11-5 methyl 3-O-benzyl-β-D-galactopyranoside 

Downstream Products

• 161953-85-1 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 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 
• 73445-27-9 methyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

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

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism

As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl

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.

AN APPROACH TO REGIOSELECTIVE ALKYLATION OF ALKYL β-D-GALACTOPYRANOSIDES THROUGH (TRIALKYLSTANNYL)ATION

Regioselective preparation of methyl 3,6-di-O-benzyl-β-D-galactopyranoside, methyl 2,4-di-O-benzyl-β-D-galactopyranoside, and mehtyl 3,4-di-O-benzyl-β-D-galactopyranoside by the stannyl method is described.