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
• Article Data: 7

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

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

Downstream Products

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

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.

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.