2,3,4-Tri-O-acetyl-6-desoxy-β-D-xylo-hex-5-enopyranosylazid | 106192-64-7

• 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-desoxy-β-D-xylo-hex-5-enopyranosylazid
• 英文别名: 2,3,4-tri-O-acetyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl azide；[(2R,3R,4S,5S)-3,5-diacetyloxy-2-azido-6-methylideneoxan-4-yl] acetate
• CAS: 106192-64-7
• 化学式: C₁₂H₁₅N₃O₇
• 分子量: 313.267
• InChiKey: NCPGAEBMIAALCG-WRWGMCAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-Tri-O-acetyl-6-desoxy-β-D-xylo-hex-5-enopyranosylazid 在 甲醇 、 sodium 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-benzyl-6-deoxy-D-xylo-hex-5-enopyranosyl azide
  参考文献：
  名称：

  Novel Synthesis of Castanospermine and 1-Epicastanospermine

  摘要：

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

  DOI：

  10.1021/ol0508577
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl azide 在 敌草腈 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 20.0h， 以86%的产率得到2,3,4-Tri-O-acetyl-6-desoxy-β-D-xylo-hex-5-enopyranosylazid
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• A General Synthesis of Iminosugars
  作者：Ciaran McDonnell、Linda Cronin、Julie L. O'Brie、Paul V. Murphy

  DOI：10.1021/jo035763u

  日期：2004.5.1

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

  DOI：——

  日期：——