40010-11-5

Basic information

• Product Name: methyl α-D-galactopyranoside 3-benzyl ether
• CAS NO: 40010-11-5
• Molecular Weight: 284.309
• Mol File: 40010-11-5.mol
• Article Data: 33

Chemical Properties

• CAS DataBase Reference: methyl α-D-galactopyranoside 3-benzyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: methyl α-D-galactopyranoside 3-benzyl ether(40010-11-5)
• EPA Substance Registry System: methyl α-D-galactopyranoside 3-benzyl ether(40010-11-5)

Safety Data

• Hazardous Substances Data: 40010-11-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 13996-88-8 3-O-benzyl-4,6-O-ethylidene-1,2-O-isopropylidene-α-D-galactopyranose 
• 3396-99-4 methyl α-D-galactopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 81348-28-9 3-O-benzyl-D-galactose 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 709-50-2 methyl beta-D-glucopyranoside 

Downstream Products

• 121312-52-5 methyl 3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranoside 
• 566197-59-9 methyl 3-O-benzyl-6-O-tosyl-β-D-glucopyranoside 
• 945621-50-1 O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl)phosphonic acid 
• 945621-52-3 dibenzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl)phosphate 
• 945621-54-5 O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl) ((4-acetamidophenyl)(hydroxy)methyl)phosphonate 
• 945621-56-7 O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl) (phenylmethyl)phosphonate 
• 945621-58-9 O-benzyl O-(1-O-methyl-2,4,6-tri-O-acetyl-β-D-galactopyranos-3-yl) ((4-acetamidophenyl)methyl)phosphonate 
• 51754-94-0 Methyl-3-O-benzyl-2-O-methyl-6-O-triphenylmethyl-α-D-glucopyranosid 

Relevant articles and documents

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.

Highly Efficient Selective Benzylation of Carbohydrates Catalyzed by Iron(III) with Silver Oxide and Bromide Anion as Co-catalysts

A highly efficient, green, and regioselective method for the benzylation of diols and polyols was developed. With the use of Ag2O (0.6 equiv.) and tetrabutylammonium bromide (0.1 equiv.) as co-catalysts, the iron(III)-catalyzed benzylation reaction proceeded to completion at 40 °C within 2–3 h and gave the products in high yields with high regioselectivities. A mechanism involving the principle of enhanced basicity of Ag2O by soft anions was proposed.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.