114853-38-2

Basic information

• Product Name: .beta.-L-Galactopyranoside, methyl 6-deoxy-1-thio-
• Synonyms: .beta.-L-Galactopyranoside, methyl 6-deoxy-1-thio-
• CAS NO: 114853-38-2
• Molecular Formula: C₇H₁₄O₄S
• Molecular Weight: 194.25
• Mol File: 114853-38-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-L-Galactopyranoside, methyl 6-deoxy-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-L-Galactopyranoside, methyl 6-deoxy-1-thio-(114853-38-2)
• EPA Substance Registry System: .beta.-L-Galactopyranoside, methyl 6-deoxy-1-thio-(114853-38-2)

Safety Data

• Hazardous Substances Data: 114853-38-2(Hazardous Substances Data)

Upstream product

• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 7404-35-5 2,3,4-tri-O-acetyl-α/β-L-fucopyranosyl acetate 
• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 80483-13-2 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 107802-80-2 (2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran 
• 858129-86-9 methyl 3,4-O-(α-ethoxybenzylidene)-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 858129-88-1 methyl 4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 858129-89-2 methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 858129-90-5 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl bromide 
• 858129-92-7 methyl 4-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl-(1->3)-4-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 186967-60-2 C₅₅H₇₆O₂₀ 
• 151669-18-0 Methyl endo-3,4-O-benzylidene-2-O-methyl-1-thio-β-L-fucopyranoside 
• 172325-31-4 methyl 2,3-di-O-benzyl-1-thio-β-L-fucopyranoside 
• 151669-19-1 Methyl 4-O-benzyl-2-O-methyl-1-thio-β-L-fucopyranoside 

Relevant articles and documents

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

Synthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2'-fucosyllactose, as a substrate of α-L-fucosidases

Four 5-thio-L-fucose-containing disaccharides having α(1→6), α(1→3), α(1→4)GlcNAc, and α(1→2)Gal linkages (compounds 1-4, respectively) were synthesized as potential α-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3·OEt2 as a catalyst gave mainly α-linked disaccharides. Only α(1→2)-linked disaccharide 4 showed inhibitory activity (K(i) = 0.21 mM) against Bacillus α-L-fucosidase which hydrolyzes the Fucα(1→2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K(i) = 30-91 μM) against bovine epididymis α-L-fucosidase.

Synthesis of α-D-Manp-(1->3)-4)>-6)>-β-D-Manp-(1->4)-β-D-GlcpNAc-(1->4)-6)>-D-GlcpNAc, a core glycoheptaose of a "bisected" complex-type glycan of glycoproteins

A synthesis of α-D-Manp-(1->3)-4)>-6)>-β-D-Manp-(1->4)-β-D-GlcpNAc-(1->4)-6)>-D-GlcpNAc was achieved by employing benzyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-O-(2-O-benzyl-β-D-

Total synthesis of X hapten, III3 Fuc alpha-nLc4 Cer.

Total synthesis of O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L- fucopyranosyl- (1----3)]-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta- D- galactopyranosyl- (1----4)-O-beta-D-glucopyranosyl-(1----1)-2-N-tetracosanoyl-(2S,3R ,4E)- sphinge

A Through-process for the Preparation of Methyl Per-O-acetyl 1-Thio-glycosides from Aldoses

D-Glucose, D-galactose, D-mannose, D-xylose, L-arabinose, L-fucose, L-rhamnose, maltose, cellobiose, lactose, D-glucosamine, D-galactosamine, and D-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.