83956-33-6

Basic information

• Product Name: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester
• Synonyms: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester
• CAS NO: 83956-33-6
• Molecular Weight: 642.62
• Mol File: 83956-33-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester(83956-33-6)
• EPA Substance Registry System: O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester(83956-33-6)

Safety Data

• Hazardous Substances Data: 83956-33-6(Hazardous Substances Data)

Upstream product

• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 83025-11-0 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate 
• 21209-51-8 N-(Benzyloxycarbonyl)-L-serin-benzylester 
• 110797-30-3 Ethyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-1-thio-β-D-galactopyranosid 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 183801-48-1 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(pyridin-2-ylsulfanylcarbonyloxy)-tetrahydro-pyran-4-yl ester 
• 167939-15-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 

Downstream Products

• 17041-36-0 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-serin 
• 83956-37-0 3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 
• 60280-57-1 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine 

Relevant articles and documents

Stereoselective synthesis of natural and non-natural thomsen-nouveau antigens and hydrazide derivatives

A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (～100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

Synthesis of clustered D-GalNAc (Tn) and D-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold

The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines.

Building Units of Oligosaccharides, LXXXVI1). - Glycosidation with Thioglycosides of Oligosaccharides to Segments of O-Glycoproteins.

In the presence of dimethyl(methylthio)sulfonium triflate (DMTST) thioglycosides of mono-, di-, tri-, and tetrasaccharides, which contain a 2-azido-2-deoxy-D-galactose as reducing unit, can react with the hydroxy group of selectively blocked derivatives of L-serine.These reactions yield the corresponding O-glycosides.Preferentially the α-glycosidically bound products will be obtained.In this way the trisaccharide glycoside 46 was prepared, which represents the core-II structure of mucins α-glycosidically linked to L-serine.Methyl triflate as promoter of this thioglycosidation is less efficient than DMTST.