Pular para o conteúdo
Merck
Todas as fotos(1)

Documentos Principais

Visualizar Toda a Documentação

513997

Sigma-Aldrich

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

Sinônimo(s):

NSC 272456

Faça loginpara ver os preços organizacionais e de contrato
Todas as fotos(1)

About This Item

Fórmula empírica (Notação de Hill):
C14H19N3O9
Número CAS:
13992-25-1
Peso molecular:
373.32
Número MDL:
MFCD00181721
Código UNSPSC:
12352200
ID de substância PubChem:
24873728
NACRES:
NA.22

forma

solid

atividade óptica

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

adequação da reação

reaction type: click chemistry

pf

127-131 °C (lit.)

cadeia de caracteres SMILES

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

chave InChI

NHNYHKRWHCWHAJ-MBJXGIAVSA-N

Aplicação

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
06627BA

Não está vendo a versão correta?

Se precisar de uma versão específica, você pode procurar um certificado específico pelo número do lote ou da remessa.

Pesquise por COA

Já possui este produto?

Encontre a documentação dos produtos que você adquiriu recentemente na biblioteca de documentos.

Visite a Biblioteca de Documentos

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
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)

Nossa equipe de cientistas tem experiência em todas as áreas de pesquisa, incluindo Life Sciences, ciência de materiais, síntese química, cromatografia, química analítica e muitas outras.

Entre em contato com a assistência técnica