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513997

Sigma-Aldrich

1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate

Synonym(s):

NSC 272456

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About This Item

Empirical Formula (Hill Notation):
C14H19N3O9
CAS Number:
13992-25-1
Molecular Weight:
373.32
MDL number:
MFCD00181721
UNSPSC Code:
12352200
PubChem Substance ID:
24873728
NACRES:
NA.22

form

solid

optical activity

[α]/D -29°, c = 1% in H2O
[α]/D -30°, c = 1% in chloroform

reaction suitability

reaction type: click chemistry

mp

127-131 °C (lit.)

SMILES string

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

InChI

1S/C14H19N3O9/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)16-17-15/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14-/m1/s1

InChI key

NHNYHKRWHCWHAJ-MBJXGIAVSA-N

Application

1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate can be used as a reactant to synthesize:
  • 1,2,3-Triazole-boron dipyrromethenes (BODIPYs) containing glucose groups via Cu(I)-catalyzed azide–alkyne ″click″ cycloaddition reaction conditions.
  • 1-(β-D-glycosyl)-5-benzenesulfonamide-1,2,3-triazole derivatives by ruthenium-catalyzed azide-alkyne cycloaddition reactions.
  • 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylamine by palladium catalyzed hydrogenation reaction.
  • Glycoside annulated dihydropyrimidinone derivatives by one-pot five-component condensation reaction with tert-butyl β-ketoester, arylaldehyde, urea and propargyl alcohol.

Reactant for:
  • Synthesis of Protein Tyrosine Phosphatase 1B inhibitor
  • Synthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition
  • Synthesis of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase
  • Hydrogenation reactions
  • Preparation of posttranslationally modified peptides efficiently mimicking neoantigens in relation to autoimmune disease

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

513997-1G:
513997-VAR:
513997-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
06627BA

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Hosahalli P Hemantha et al.
Organic & biomolecular chemistry, 9(8), 2597-2601 (2011-03-09)
Palladium nanoparticles supported over poly(vinyl)chloride matrix (PVC-Pd(0)) are prepared through an efficient and inexpensive protocol. The catalyst has been characterized by XRD, SEM and TEM and its utility for the reduction of a range of functional groups as well as
A facile one-pot five-component synthesis of glycoside annulated dihydropyrimidinone derivatives with 1, 2, 3-triazol linkage via transesterification/Biginelli/click reactions in aqueous medium
Rao GB Dharma, et al.
Tetrahedron Letters, 55(1) (2014)
Syntheses of 1, 2, 3-triazole-BODIPYs bearing up to three carbohydrate units
Nguyen AL, et al.
New. J. Chem., 42(10) (2018)
Adam J Salmon et al.
Bioorganic & medicinal chemistry letters, 21(20), 6058-6061 (2011-09-10)
Carbonic anhydrase IX (CA IX) is a recently validated target for the development of new cancer therapies. In this Letter we describe the synthesis and CA inhibition of a novel series of carbohydrate-based 1,5-disubstituted-1,2,3-triazole benzenesulfonamides. The key step of our

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