358681-69-3

Upstream product

• 106-45-6 para-thiocresol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 83-87-4 D-Mannose pentaacetate 
• 13242-53-0 acetobromomannose 

Downstream Products

• 1320281-33-1 p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 1320281-34-2 methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate) 
• 1141493-91-5 C₂₅H₅₀O₅SSi₄ 
• 1235137-39-9 p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1320281-40-0 p-tolyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 676260-28-9 p-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 676260-44-9 p-methylphenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-β-D-mannopyranoside 
• 676260-43-8 p-methylphenyl 3-O-p-methoxybenzyl-1-thio-β-D-mannopyranoside 
• 676260-42-7 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triol 

Relevant academic research and scientific papers

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.

Mannopyranosyl uronicaAcid donor reactivity

The reactivity of a variety of mannopyranosyl uronic acid donors was assessed in a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-β-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-α-(S)-tolyl mannose.

Novel efficient routes to heparin monosaccharides and disaccharides achieved via regio- and stereoselective glycosidation

A new methodology for the synthesis of heparin building blocks has been developed. We describe novel efficient routes to both L-iduronic acid and D-glucuronic acid acceptors. Glycosylation with thioglycosides donors gave corresponding disaccharides in a regio- and stereoselective fashion. An improved approach to synthesizing azido-glucose thioglycoside donor to render azido-sugar from mannose via nucleophilic substitution is described.