97205-08-8

Usage

Uses

Used in Carbohydrate Synthesis:
Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is used as a key intermediate in the synthesis of various carbohydrates and their derivatives. Its protected structure allows for selective deprotection and further functionalization, making it a versatile building block for the preparation of complex carbohydrate structures.
Used in Macromolecule Synthesis:
In the field of macromolecule synthesis, Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is used as a component in the construction of larger carbohydrate-containing structures, such as polysaccharides and glycoconjugates. Its protected nature enables the controlled assembly of these macromolecules, facilitating the development of advanced materials with specific properties and functions.
Used in Pharmaceutical Industry:
Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is used as a synthetic building block in the development of pharmaceutical compounds, particularly those targeting carbohydrate-binding receptors or enzymes. Its well-defined structure and ease of modification make it an attractive candidate for the design of novel therapeutic agents with improved efficacy and selectivity.
Used in Materials Science:
In materials science, Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is employed in the design and synthesis of carbohydrate-based materials, such as hydrogels, nanoparticles, and self-assembled structures. These materials have potential applications in drug delivery, tissue engineering, and biosensing, owing to their unique properties and interactions with biological systems.

Upstream product

• 100-39-0 benzyl bromide 
• 155-30-6 methyl 1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 160636-38-4 per-O-benzylated methyl α-thiogalactopyranoside 

Downstream Products

• 107855-20-9 benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 107855-19-6 benzyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 113421-46-8 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 113421-45-7 Benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 99388-26-8 benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 107855-18-5 benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-glucopyranoside 
• 129163-39-9 4-methoxyphenyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 129163-34-4 4-methoxyphenyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 53081-30-4 tetra-O-benzyl-α-D-galactosyl bromide 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 67145-38-4 2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl bromide 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 160636-38-4 per-O-benzylated methyl α-thiogalactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds

Treatment of 'armed' methyl thiogalactosides with iodine in the absence of an acceptor alcohol results in thioglycoside epimerisation, whereas there is no effect on the corresponding 'disarmed' methyl thioglycosides. In contrast, iodine-hexamethyldisilane (which generates iodotrimethylsilane in situ) brings about epimerisation of 'disarmed' thioglycosides, ultimately giving rise to the corresponding α-glycosyl iodides on extended exposure. Cross-over experiments show the former iodine-promoted epimerisation process to be intermolecular, whereas the latter iodine-hexamethyldisilane-promoted epimerisation is intramolecular. Treatment of the same methyl thiogalactosides with iodine monobromide gives rise to the thermodynamically favoured α-glycosyl bromides, whereas reaction with iodine monochloride initially gives the kinetic β-glycosyl chlorides, which slowly epimerise to the thermodynamic α-linked products. Differences in the outcome of thioglycoside activation by I-I, I-Br and I-Cl suggest there may be scope for influencing the stereochemical course of thioglycoside-based glycosylation reactions through careful choice of promoter. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis and two-dimensional nuclear magnetic resonance analysis of a tetra- and a hexa-saccharide fragment of the O-specific polysaccharide of Shigella dysenteriae type 1

The synthesis of the tetra- and hexa-succharide methyl glycosides α-D-Galp-(1-->3)-α-D-GlcpNAc-(1-->3)-α-L-Rhap-(1-->3)-α-L-Rhap-OMe (1), and α-L-Rhap-(1-->3)-α-L-Rhap-(1-->2)-α-D-Galp-(1-->3)-α-D-GlcpNAc-(1-->3)-α-L-Rhap-(1-->3)-α-L-Rhap-OMe (3) is descr

Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide.

Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate, O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha (and beta)-D-glucopyranosyl fluoride, and O-(2,3,4,6-tetra-O-acetyl-alpha-D -galactopyranosyl)-(1----3)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyran osyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate.

A SYNTHESIS OF 8-METHOXYCARBONYLOCT-1-YL O-α-D-GALACTOPYRANOSYL-(1->3)-O-β-D-GALACTOPYRANOSYL-(1->4)-2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSIDE

Halide assised glycosylation, using a non-participating 2-substituent (benzyl) in the glycosyl halide, was used to obtain the α-D-galactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the β-D-gala