84635-53-0

Upstream product

• 917-64-6 methyl magnesium iodide 
• 158419-93-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl thiocyanate 
• 88104-27-2 methyl-(1-thio-α-L-arabinopyranoside) 
• 108-24-7 acetic anhydride 
• 624-92-0 Dimethyldisulphide 
• 14227-79-3 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl iodide 
• 87-72-9 L-(+)-arabinose 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 106-45-6 para-thiocresol 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose 
• 51830-02-5 bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside 
• 26385-24-0 potassium methanethiolate 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 

Downstream Products

• 88104-27-2 methyl-(1-thio-α-L-arabinopyranoside) 

Relevant academic research and scientific papers

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.

A facile and efficient method for the one-pot synthesis of per-O-acetylated thioglycosides from unprotected sugars

An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.

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.

Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides

Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.