211801-76-2

Upstream product

• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 106-45-6 para-thiocresol 
• 1772-03-8 D-(+)-galactosamine hydrochloride 

Downstream Products

• 100929-00-8 benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 
• 125760-22-7 p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside 
• 125760-23-8 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 139608-16-5 methyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1380218-26-7 6-chlorohexyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranoside 
• 1380218-24-5 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-D-galactopyranosyl-β-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1380218-22-3 methyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-2,3-O-isopropylidene-1-α-L-rhamnopyranoside 
• 1380218-33-6 p-tolyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-galactopyranside 
• 1334599-14-2 2-azido-3,4-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactopyranose-1-O-methylthioglycoside 
• 1334599-51-7 N-(9-fluorenylmethoxycarbonyl)-O-[4,5-di-O-benzoyl-3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl]-L-serine benzyl ester 
• 1334599-48-2 N-benzyloxycarbonyl-O-[4,5-di-O-benzoyl-3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl]-L-threonine benzyl ester 
• 1334599-45-9 N-benzyloxycarbonyl-O-[4,5-di-O-benzoyl-3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl]-L-serine benzyl ester 
• 1334599-12-0 C₃₃H₃₉N₃O₆SSi 
• 1334599-37-9 methyl 4,5-di-O-acetyl-3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Chondroitin sulfate oligosaccharides and preparation method and applications thereof

The invention discloses a series of chondroitin sulfate oligosaccharides as shown in a formula and a preparation method and biological activity thereof, and intermediates and a synthesis method of theintermediates. The key points of the invention are as f

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

Application of 2-azido-2-deoxythioglycosides for β-glycoside formation and oligosaccharide synthesis

Most natural 2-acetamido-2-deoxyglycosides exist in a 1,2-trans-β- glycosidic configuration. This study investigated the use of 2-azido-2-deoxythioglycosides for 1,2-trans-β-glycosidic bond formation under low-concentration glycosylation conditions. Furth

Study of the stereoselectivity of 2-azido-2-deoxygalactosyl donors: Remote protecting group effects and temperature dependency

The stereoselectivity of glycosylation reactions is affected by many factors. Synthesis of 1,2-cis glycosidic linkages (such as α linkages in glucose and galactose like monosaccharides) is challenging due to lack of control of the stereoselectivity. Our s

Development of highly stereoselective GalN3 donors and their application in the chemical synthesis of precursors of Tn antigen

Two GalN3 thioglycoside donors were designed and prepared based on protecting group-stereoselectivity relationship study for optimum alpha selectivity. These donors showed excellent stereoselectivity in test reactions with various acceptors and were successfully applied in the synthesis of precursors for Tn antigen and a core structure of O-glycan.

Sugar-assisted ligation in glycoprotein synthesis

Sugar-assisted ligation (SAL) presents an attractive strategy for the synthesis of glycopeptides, including the synthesis of cysteine-free β-O-linked and N-linked glycopeptides. Here we extended the utility of SAL for the synthesis of α-O-linked glycopeptides and glycoproteins. In order to explore SAL in the context of glycoprotein synthesis, we developed a new chemical synthetic route for the α-O-linked glycoprotein diptericin ε. In the first stage of our synthesis, diptericin segment Cys(Acm) 37-Gly52 and segment Val53-Phe82 were assembled by SAL through a Gly-Val ligation junction. Subsequently, after Acm deprotection, diptericin segment Cys37-Phe82 was ligated to segment Asp1-Asn36 by means of native chemical ligation (NCL) to give the full sequence of diptericin ε. In the final synthetic step, hydrogenolysis was applied to remove the thiol handle from the sugar moiety with the concomitant conversion of mutated Cys37 into the native alanine residue. In addition, we extended the applicability of SAL to the synthesis of glycopeptides containing cysteine residues by carrying out selective desulfurization of the sulfhydryl-modified sugar moiety in the presence of acetamidomethyl (Acm) protected cysteine residues. The results presented here demonstrated for the first time that SAL could be a general and useful tool in the chemical synthesis of glycoproteins.

Anomeric reactivity-based one-pot oligosaccharide synthesis: A rapid route to oligosaccharide libraries

The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing a one-pot sequential approach. With the help of the anomeric reactivity values of thioglycosides, using a thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor and donor coupled with another fully protected thioglycoside, a di- or trisaccharide is selectively formed without self-condensation and subsequently reacted in situ with an anomerically inactive glycoside (mono- or disaccharide) to form a tri- or tetrasaccharide in high overall yield. The approach enables the rapid assembly of 33 linear or branched fully protected oligosaccharides using designed building blocks. These fully protected oligosaccharides have been partially or completely deprotected to create 29 more structures to further increase the diversity of the library.