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514004

Sigma-Aldrich

1-Azido-1-deoxy-β-D-glucopyranoside

Synonym(s):

Β-D-Glycopyranosyl azide, 1-Azido-1-deoxy-beta-D-glucose

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About This Item

Empirical Formula (Hill Notation):
C6H11N3O5
CAS Number:
20379-59-3
Molecular Weight:
205.17
MDL number:
MFCD03701503
UNSPSC Code:
12352201
PubChem Substance ID:
24873730
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

reaction type: click chemistry

mp

60-65 °C (lit.)

SMILES string

OC[C@H]1O[C@@H](N=[N+]=[N-])[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C6H11N3O5/c7-9-8-6-5(13)4(12)3(11)2(1-10)14-6/h2-6,10-13H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChI key

KSRDTSABQYNYMP-VFUOTHLCSA-N

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Application

1-Azido-1-deoxy-β-D-glucopyranoside can be used as an organic building block to prepare:
  • 1,2,3-triazole-containing (1-azido-1-deoxy-β-D-glucopyranoside) complex by reacting with propagylglycine and sodium ascorbate via copper-catalyzed click chemistry approach.
  • D-glucose-mercaptoacetyl triglycine (MAG3) derivative applicable as a potent tumor diagnosis agent.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S K Sinha et al.
Carbohydrate research, 81(2), 239-247 (1980-03-15)
Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion
André Luís Branco de Barros et al.
Bioorganic & medicinal chemistry letters, 19(9), 2497-2499 (2009-04-01)
A d-glucose-MAG(3) derivative was successfully synthesized and radiolabeled in high labeling yield. Biodistribution studies in Ehrlich tumor-bearing mice were performed. This compound showed high accumulation in tumor tissue with high tumor-to-muscle ratio and moderate tumor-to-blood ratio. Thus, d-glucose-MAG(3) is a
IrfanUllah Khan et al.
Pakistan journal of pharmaceutical sciences, 29(1), 213-219 (2016-02-02)
The 1,2,3-triazole-containing (1-azido-1-deoxy-β-D-glucopyranoside) complex was synthesized using click chemistry approach and evaluated its potential as a tumor-seeking agent. In the present study, (99m)Tc-tricarbonyl labeled (1-azido-1-deoxy-β-D-glucopyranoside) radiotracer [(99m)Tc(CO)(3)-BM], (where BM stands for biomolecule, e.g., (1-azido-1-deoxy-β-D- glucopyranoside)) was synthesized via click chemistry

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