97205-08-8

Basic information

• Product Name: Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside
• Synonyms: Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside;Methyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside
• CAS NO: 97205-08-8
• Molecular Formula: C₃₅H₃₈O₅S
• Molecular Weight: 570.74
• Mol File: 97205-08-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside(97205-08-8)
• EPA Substance Registry System: Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside(97205-08-8)

Safety Data

• Hazardous Substances Data: 97205-08-8(Hazardous Substances Data)

Usage

Description

Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is a synthetic oligosaccharide that is structurally similar to naturally occurring carbohydrates. It is characterized by the presence of a methyl group and four benzyl groups attached to the sugar molecule, which provide protection and stability during chemical reactions. Methyl2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside is commonly used as a building block in the synthesis of complex carbohydrates and macromolecules, such as the triglycosylated rhamnoside fragment of rhamnogalacturonan-II side chain A.

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

• 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 
• 100-39-0 benzyl bromide 
• 155-30-6 methyl 1-thio-β-D-galactopyranoside 

Downstream Products

• 41671-29-8 6-O-(tetra-O-benzyl-β-D-galactopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 41671-29-8 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 246516-65-4 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide 
• 146453-40-9 O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-galactopyranosyl fluoride 
• 97205-09-9 methyl O-acetyl-2,6-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 
• 97205-10-2 C₅₆H₅₅BrO₁₃ 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 252845-51-5 N-acetyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 635302-03-3 1-azido-3,6-dioxa-8-octyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside 
• 725250-84-0 Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 144069-06-7 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 144069-05-6 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 274258-29-6 2-[2-(2-chloroethoxy)ethoxy]ethyl 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-β-D-galactopyranoside 

Relevant articles and documents

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.

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.