20379-59-3

Basic information

• Product Name: 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 1-azido-1-deoxy-β-d-glucopyranoside;b-D-Glucopyranosylazide;4-azido-4-deoxyglucose;beta-D-Glucopyranosyl azide;4-Azido-4-deoxy-beta-D-glucose;β-D-Glucopyranosyl azide ,98%;β-D-Glucopyranosyl azide;1-Azido-1-deoxy-beta-D-glucopyranoside min. 98%
• CAS NO: 20379-59-3
• Molecular Formula: C₆H₁₁N₃O₅
• Molecular Weight: 205.17
• Product Categories: Carbohydrate Synthesis;Click Chemistry;MonosaccharidesChemical Ligation;Organic Azides;Specialty Synthesis;Carbohydrates
• Mol File: 20379-59-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 60-65 °C(lit.)
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE(20379-59-3)
• EPA Substance Registry System: 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE(20379-59-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 20379-59-3(Hazardous Substances Data)

Usage

General Description

1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is a chemical compound used in biochemical and glycosylation studies. It is a derivative of glucose that contains an azide functional group. 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is commonly used as a precursor in the synthesis of glycoconjugates and as a substrate for enzymes such as glycosidases and glycosyltransferases. It is also used in the development of glycoarrays for the study of carbohydrate-protein interactions and in the preparation of glycoprotein mimics for drug discovery and vaccine development. The azido group in 1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE allows for selective bioorthogonal labeling and functionalization of glycoconjugates in biological systems, making it a valuable tool in chemical biology and glycobiology research.

InChI:InChI=1/C6H11N3O5/c7-9-8-5(3(12)1-10)6(14)4(13)2-11/h2-6,10,12-14H,1H2/t3-,4+,5-,6-/m1/s1

Upstream product

• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 50-99-7 D-glucose 
• 20379-61-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 2280-44-6 D-Glucose 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 4132-27-8 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranose 
• 4490-93-1 N-(2-phenylethylaminocarbonyl)-β-D-glucopyranosylamine 
• 725740-10-3 N-(benzylaminocarbonyl)-β-D-glucopyranosylamine 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 160712-36-7 (2R,3R,4S,5S,6R)-2-Azido-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 
• 7284-37-9 D-glucopyranosyl amine 
• 6009-45-6 β-D-glucopyranosylamine 1,2-(cyclic carbamate) 
• 1610473-05-6 1-(β-D-glucopyranosyl)-4-(4-nitrophenyl)-1,2,3-triazole 

Relevant articles and documents

Switching between X-Pyrano-, X-Furano-, and Anhydro- X-pyranoside Synthesis (X = C, N) under Lewis acid Catalyzed Conditions

A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)3) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides), or are virtually unknown (anhydro-C-pyranosides), which mechanistically arise from whether a direct substitution, isomerization/substitution, or substitution/isomerization occurs, respectively.

Direct azidation of unprotected carbohydrates under Mitsunobu conditions using hydrazoic acid

A single step procedure for the direct and regioselective synthesis of carbohydrate azides from unprotected sugars using hydrazoic acid under Mitsunobu conditions is reported. A series of mono-, di-, or triazido polyhydroxylated systems are described.

Synthetic studies on nephritogenic glycosides. Synthesis of N-(β-L-aspartyl)-α-D-glucopyranosylamine

-