2595-43-9

Upstream product

• 17314-32-8 tributyl(methylthio)stannane 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 624-92-0 Dimethyldisulphide 
• 793696-63-6 2,3,4-tri-O-acetyl-α-D-xylopyranosyl iodide 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 87-72-9 D-Xylose 
• 3908-55-2 Trimethyl(methylthio)silane 
• 2595-45-1 Methyl 1-thio-β-D-xylopyranoside 
• 108-24-7 acetic anhydride 
• 50837-92-8 2,3,4-tri-O-acetyl-D-xylopyranosyl bromide 

Downstream Products

• 2595-45-1 Methyl 1-thio-β-D-xylopyranoside 
• 808137-29-3 C₄₄H₅₀O₁₆ 
• 132278-39-8 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 
• 130450-83-8 Benzyl 2,3,6-tri-O-benzyl-4-O-<2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-xylopyranosyl>-β-D-glucopyranoside 
• 130450-86-1 Benzyl 2,3,6-tri-O-benzyl-4-O-<2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-β-D-xylopyranosyl>-β-D-glucopyranoside 
• 130450-90-7 Methyl 2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-xylopyranoside 
• 130450-84-9 benzyl O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 130450-89-4 Methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-xylopyranoside 
• 130450-88-3 Methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-xylopyranoside 
• 130450-81-6 Methyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-1-thio-β-D-xylopyranoside 
• 130450-79-2 Methyl 2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-1-thio-β-D-xylopyranoside 
• 130450-80-5 Methyl 4-O-(p-methoxybenzyl)-1-thio-β-D-xylopyranoside 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of n-hexyl and O-β-D-xylopyranosyl-(1→6) -β-D-glucopyranosides

Direct β-glucosidation between 1,6-octanediol (5) and D-glucose (3) using the immobilized β-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave a mono-β-glucoside (6) in 61.4% yield, which was converted into the n-hexyl β-D

Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

Synthesis of O-alpha-D-glucopyranosyl-(1----4)-O-alpha -D-xylopyranosyl-(1----4)-O-alpha -D-xylopyranosyl-(1----4)-D-glucopyranose as a substrate analogue of alpha amylase.

The tetrasaccharide a-D-Glcp-(1----4)-a-D-Xylp-(1----4)-a-D-Xylp-(1----4)-D- Glcp (1) has been synthesized, as a substrate analogue of alpha amylase, by silver perchlorate-catalyzed glycosylation of benzyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-a-D-xylopyranosyl)-beta-D- glucopyranoside (30) with 2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-a-D- glucopyranosyl)-a-D-xylopyranosyl chloride or by methyl triflate-promoted condensation of 30 with methyl 2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-a-D-glucopyranosyl)-1-thio- beta-D-xylopyranoside, followed by removal of protecting groups of the resulting tetrasaccharide derivative 40.

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.