513997

1-叠氮-1-脱氧-β-D-吡喃葡萄糖苷四乙酸酯

• 同義詞: NSC 272456
• 經驗公式（希爾表示法）: C₁₄H₁₉N₃O₉
• CAS號碼: 13992-25-1
• 分子量：: 373.32
• MDL號碼: MFCD00181721
• 分類程式碼代碼: 12352200
• PubChem物質ID: 24873728
• NACRES: NA.22

屬性

• 形狀: solid
• 光學活性: [α]/D -29°, c = 1% in H₂O; [α]/D -30°, c = 1% in chloroform
• 反應適用性: reaction type: click chemistry
• mp: 127-131 °C (lit.)
• SMILES 字串: 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 密鑰: NHNYHKRWHCWHAJ-MBJXGIAVSA-N

描述

應用

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

安全資訊

• 儲存類別代碼: 11 - Combustible Solids
• 水污染物質分類（WGK）: WGK 3
• 閃點（°F）: Not applicable
• 閃點（°C）: Not applicable
• 個人防護裝備: Eyeshields, Gloves, type N95 (US)