166907-09-1

Basic information

• Product Name: Benzyl 2-Azido-2-deoxy-α-D-galactopyranoside
• Synonyms: Benzyl 2-Azido-2-deoxy-α-D-galactopyranoside;PhenylMethyl 2-Azido-2-deoxy-α-D-galactopyranoside;Benzyl 2-azido-2-deoxy-a-D-galactopyranoside
• CAS NO: 166907-09-1
• Molecular Formula: C13H17N3O5
• Molecular Weight: 295.29118
• Product Categories: Aromatics;Carbohydrates & Derivatives
• Mol File: 166907-09-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, DMSO, Methanol
• CAS DataBase Reference: Benzyl 2-Azido-2-deoxy-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-Azido-2-deoxy-α-D-galactopyranoside(166907-09-1)
• EPA Substance Registry System: Benzyl 2-Azido-2-deoxy-α-D-galactopyranoside(166907-09-1)

Safety Data

• Hazardous Substances Data: 166907-09-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C13H17N3O5/c14-16-15-10-12(19)11(18)9(6-17)21-13(10)20-7-8-4-2-1-3-5-8/h1-5,9-13,17-19H,6-7H2/t9?,10-,11-,12+,13-/m0/s1

Upstream product

• 80321-89-7 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose 
• 2873-29-2 D-glucal triacetate 
• 100-51-6 benzyl alcohol 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 
• 95451-80-2 Benzyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-mannopyranosid 
• 68733-05-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate 
• 20194-18-7 sodium phenyl-methanolate 
• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 68733-05-1 peracetylated α-glycosyl nitrate 2-azido-2-deoxy-D-galactopyranose 

Downstream Products

• 484-57-1 (R)-2-(((3R,4R,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid 
• 79633-18-4 neocarzinostatin chromophore 

Relevant articles and documents

Peptidoglycan Modifications Tune the Stability and Function of the Innate Immune Receptor Nod2

Natural modifications of peptidoglycan modulate the innate immune response. Peptidoglycan derivatives activate this response via the intracellular innate immune receptor, Nod2. To probe how these modifications alter the response, a novel and efficient carbohydrate synthesis was developed to allow for late-stage modification of the amine at the 2-position. Modification of the carbohydrate was found to be important for stabilizing Nod2 and generating the proper response. The native Nod2 ligands demonstrate a significant increase in the cellular stability of Nod2. Moreover, changing the identity of the natural ligands at the carbohydrate 2-position allows for the Nod2-dependent immune response to be either up-regulated or down-regulated. The ligand structure can be adjusted to tune the Nod2 response, suggesting that other innate immune receptors and their ligands could use a similar strategy.

SYNTHETIC N-ACETYL-MURAMIC ACID DERIVATIVES AND USES THEREOF

The present invention provides N-acetyl-muramic acid (NAM) derivatives having Formula I, wherein Xa is selected from the group consisting of X1-X59, Ya is selected from the group consisting of H, monophosphate, uridine diphosphate and ethyl azide linker prepared from 2-azido-ethanol, and Za is selected from the group consisting of OH, an ethylene diamine coupled fluorophore, a peptide and a peptide with an ethylene diamine coupled fluorophore, wherein the peptide is selected from the group consisting of a monopeptide, a dipeptide, a tripeptide and a pentapeptide. Also provided are methods for synthesizing NAM derivatives and methods for modulating Nod2 in cells, modifying bacterial cell wall or modulating innate immune response by a subject to bacterial cells upon exposure to NAM derivatives.

Chemical synthesis of the desialylated human Cad-anti-genic determinant.

Benzyl 2-azido-2-deoxy-beta-D-galactopyranoside was converted into benzyl 2-azido-4,6-O-benzyl-2-deoxy-beta-D-galactopyranoside via benzylidenation, p-methoxybenzylation, acid hydrolysis, benzylation, and selective oxidation. Condensation of 1,2,3,4,6-pen

ERPROBTE SYNTHESE VON 2-AZIDO-2-DESOXY-D-MANNOSE UND 2-AZIDO-2-DESOXY-D-MANNURONSAEURE ALS BAUSTEIN ZUM AUFBAU VON BAKTERIEN-POLYSACCHARID-SEQUENZEN

The azidonitration of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol at low temperature afforded preponderantly the azidonitrate having the D-manno configuration.After reaction with sodium acetate, 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose was directly isolated and deblocking gave 2-azido-2-deoxy-D-mannopyranose. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide and 2-azido-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide were prepared and are suitable for selective α- and β-glycoside synthesis.In the presence of platinum-oxygen, the catalytic oxidation of benzyl 2-azido-2-deoxy-α-D-mannopyranoside gave in high yields (benzyl 2-azido-2-deoxy-α-D-mannopyranosid)uronic acid from which 2-amino-2-deoxy-D-mannopyranuronic acid was obtained.By catalytic oxidation, selectively blocked derivatives of 2-amino-2-deoxy-D-mannopyranose were converted into the correspondind uronic acid derivatives.

SYNTHESE EINER DISACCHARIDEINHEIT AUS N-ACETYL-NEURAMINSAEURE UND 2-ACETAMIDO-2-DESOXY-D-GALACTOSE

The reaction of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chloride)onate with benzyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-galactopyranoside promoted by mercury cyanide-mercury bromide afforded a 1:1 m

SYNTHESIS OF TRISACCHARIDE DERIVATIVES WITH THE SEQUENCE OF THE DESIALYLATED Cad BLOOD GROUP DETERMINANT

Benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O--β-D-galactopyranoside, a close precursor of the desialylated Cad blood group determinant, has been synthesized.