210834-01-8

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 930-69-8 sodium thiophenolate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 76-83-5 trityl chloride 

Downstream Products

• 314038-33-0 phenyl 2,4-di-O-acetyl-1-thio-β-D-glucopyranoside 
• 314038-16-9 Acetic acid (2R,3R,4S,5R,6S)-5-acetoxy-4-(tert-butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 488152-98-3 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->3)]-2,4-di-O-acetyl-1-thio-β-D-glucopyranoside 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 173655-37-3 Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 158411-91-7 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 158411-90-6 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid 
• 158411-89-3 [(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-yl]-methanol 
• 120403-27-2 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 151988-23-7 Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 151988-24-8 Phenyl 2,3,4-tri-O-pivaloyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside sulfoxide 
• 210834-04-1 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside 
• 210834-06-3 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 210834-03-0 phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and absolute configuration of lepidimoide, a high potent allelopathic substance from mucilage of germinated cress seeds

Lepidimoide (1), 1,2-cis-linked dissacharide, was synthesized from D-glucose and α-L-rhamnose for determination of the absolute configuration.

Synthesis of sulfonic acid analogues of the non-reducing end trisaccharide of the antithrombin binding domain of heparin

Three sulfonic acid trisaccharides related to the antithrombin-binding DEFGH domain of heparin were synthesised. Trisaccharides carrying the sulfonatomethyl moiety at position 2 or 6 were prepared in high yields by [DE+F] couplings using the same disaccha

Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions

(Chemical Equation Presented) The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate 3H4 and

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel

Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4?SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of the crude product.

Stereoselective glycosylation and oligosaccharide synthesis on solid support using a 4-azido-3-chlorobenzyl group for temporary protection

A versatile and practical methodology for solid-phase synthesis was elaborated in the synthesis of α(1→6)- and β(1→6)linked oligoglucoses by using thioglycosides having a 4-azido-3-chlorobenzyl (ClAzb) group for temporary protection of hydroxy functions.

Highly efficient and practical synthesis of 3,6-branched oligosaccharides.

[reaction: see text] A one-pot formation of the 3- and 6-OH differentially protected sugar synthon was described. A mannopyranosyl pentasaccharide and a glucopyranosyl hexasaccharide were prepared employing this new finding.

Azidohalogenobenzyl derivatives, sugar compounds and protection of hydroxy groups

Azidohalogenobenzyl derivatives of the formula (I) STR1 wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.

Total synthesis of the nephritogenoside glycopeptide

A mild three-dimensional orthogonal protection scheme, based on Nps/Fmoc-groups for α-amino, benzyl residues for hydroxyl and carboxyl protection and 2-chlorotrityl esters as anchoring linkage proved to be a new effective approach for the synthesis of gly

Block Synthesis of Oligosaccharides under Mild Conditions

Details on a synthesis of the trisaccharide α-D-Glc(1-->6)-β-D-Glc(1-->6)-D-Glc are reported.The O-glycosidic linkages were constructed using the sulfoxide glycosylation reaction.This approach proves to be a rapid glycosylation method leading to high yield and good selectivity. - Keywords: Oligosaccharides, Phenyl 1-Thioglycoside Sulfoxides