2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide | 106192-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide
• 英文别名: 2,3,4-Tri-O-acetyl-6-desoxy-6-iod-β-D-glucopyranosylazid；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-6-azido-2-(iodomethyl)oxan-3-yl] acetate
• CAS: 106192-45-4
• 化学式: C₁₂H₁₆IN₃O₇
• 分子量: 441.179
• InChiKey: CISKIZLFYGSEQV-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide 在 碳酸氢钠 Oxone 、 1,1,1-三氟丙酮 、 ethylene diamine tetraacetic acid tetrasodium salt 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-acetyl-5,6-anhydro-5-C-hydroxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 在 叠氮基三甲基硅烷 、 硫酸 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u

文献信息

• Gyoergydeak, Zoltan; Szilagyi, Laszlo, Liebigs Annalen der Chemie, 1987, p. 235 - 242
  作者：Gyoergydeak, Zoltan、Szilagyi, Laszlo

  DOI：——

  日期：——
• GYORGYDEAK, ZOLTAN;SZILAGYI, LASZLO, LIEBIGS ANN. CHEM.,(1987) N 3, 235-241
  作者：GYORGYDEAK, ZOLTAN、SZILAGYI, LASZLO

  DOI：——

  日期：——