3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid | 85219-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid
• 英文别名: O³,O⁴,O⁶-triacetyl-β-D-glucopyranosyl azide；O³,O⁴,O⁶-Triacetyl-β-D-glucopyranosylazid；[(2R,3R,4R,5R,6R)-3,4-diacetyloxy-6-azido-5-hydroxyoxan-2-yl]methyl acetate
• CAS: 85219-64-3
• 化学式: C₁₂H₁₇N₃O₈
• 分子量: 331.282
• InChiKey: OBAFBBKADYDMOD-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid 在 吡啶 作用下， 生成 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate
  参考文献：
  名称：

  Bertho; Aures, Justus Liebigs Annalen der Chemie, 1955, vol. 592, p. 54,65

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-Tri-O-acetyl-2-O-laevulinoyl-β-D-glucopyranosylazid 在 一水合肼 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 0.17h， 以83%的产率得到3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid
  参考文献：
  名称：

  Gyoergydeak, Zoltan; Ling, Istvan; Bognar, Rezsoe, Liebigs Annalen der Chemie, 1983, # 2, p. 279 - 289

  摘要：

  DOI：

文献信息

• Synthesis of D-glycopyranosyl azides from 1,2-anhydrosugars using lithium azidohydridodiisobutylaluminate
  作者：Goo Soo Lee、Hye Kyung Min、Bong Young Chung

  DOI：10.1016/s0040-4039(98)02435-6

  日期：1999.1

  1,2-Anhydrosugars were transformed regio- and stereoselectively into the corresponding D-glycopyranosyl azides in high yield by treatment with lithium azidohydridodiisobutylaluminate in THE (C) 1998 Elsevier Science Ltd. All rights reserved.
• Ceric Ammonium Nitrate-Catalyzed Azidation of 1,2-Anhydro Sugars: Application in the Synthesis of Structurally Diverse Sugar-Derived Morpholine 1,2,3-Triazoles and 1,4-Oxazin-2-ones
  作者：Y. Suman Reddy、A. P. John Pal、Preeti Gupta、Alafia A. Ansari、Yashwant D. Vankar

  DOI：10.1021/jo200260w

  日期：2011.8.5

  Azidation of 1,2-anhydro sugars with NaN3 in CH3CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.