79781-69-4

Upstream product

• 153808-91-4 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 4098-06-0 triacetyl-D-galactal 
• 68733-26-6 2-deoxy-2-azidogalactopyranose 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 211801-76-2 p-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α/β-D-galactopyranoside 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 1310050-35-1 C₃₄H₃₅N₃O₄S 
• 90405-18-8 Allyl-2-azido-2-desoxy-β-D-galactopyranosid 
• 72605-77-7 (2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one 
• 862851-12-5 phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 

Downstream Products

• 139608-08-5 isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl carbonate 
• 139608-07-4 isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl carbonate 
• 182355-73-3 2-((2S,3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine 
• 182355-71-1 2-pyridyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-thio-α-D-galactopyranoside 
• 205593-86-8 3,4,6-tri-O-benzyl-2-deoxy-2-azido-β-D-galactopyranosyl 2,2,2-trichloroacetimidate 
• 220734-53-2 thexyldimethylsilyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranoside 

Relevant academic research and scientific papers

Reagent controlled glycosylations for the assembly of well-defined pel oligosaccharides

A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-α-(1,4)-glucosazide] disaccharide building blocks were synthesized using a 4,6-O-DTBS protected galactosyl azide donor.

Stereoselective Synthesis of 1,1′-Disaccharides by Organoboron Catalysis

The highly stereoselective synthesis of 1,1′-disaccharides was achieved by using 1,2-dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is

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.

Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of: N -glycopeptides, pseudo-trisaccharides and an iminosugar

Glycals were found to react with a reagent system comprising of phenyliodine bis(trifluoroacetate) (PIFA) and Me3SiN3 in the presence of TMSOTf as a catalyst to form the corresponding vicinal 1,2-diazides. On the other hand, they rea

Direct, microwave-assisted substitution of anomeric nitrate-esters

A series of carbohydrate 2-azido-1-nitrate-esters, protected at the C-3, C-4, and C-6 positions, were hydrolyzed thermally under reagent free conditions. This preliminary result was extended to direct exchange of the 1-nitrate-ester modality for alcohol,

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

Glycosylation using 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose, - galactose, and -mannose with the aid of p-nitrobenzenesulfonyl chloride- silver trifluoromethanesulfonate-triethylamine system

This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl- 2-deoxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6- tri-O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1 → 4)-O-α-D-mannopyranosyl- (1 → 4)-a-D-mannopyranose, the repeating unit of the main chain of the O- specific cell wall polysaccharide of E. coli 058 was synthesized.

Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapG(J)96 from Escherichia coli

The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitor 2(trimethylsilyl)ethyl (α-D-galactopyranosyl)-(1→4)- β-d-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapG(J96), using an ELISA assay. The inhibitory efficiencies (K(rel); relative to the reference inhibitor) were: 157, 13, and 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabioside.

Electrophilic Azidation of 2-Deoxy-aldono-1,5-lactones: an Alternative Route to 2-Azido-2-deoxy-aldopyranoses

Electrophilic azidation of tri-O-benzyl-2-deoxy-D-galactono-1,5-lactone 3 with triisopropylphenylsulfonyl azide, followed by selective reduction with diisobutylaluminium hydride, yielded tri-O-benzyl-2-azido-2-deoxy-D-galactopyranose 5 as the sole product

Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals

A new and efficient preparation of diversely protected 2-azido-2-deoxyglycopyranosides from the corresponding glycals is described. The glycals are first transformed into protected phenyl 2-azido-2-deoxy-selenoglycopyranosides by azido-phenylselenylation.