tert-butyl (7S,8R)-8-acetyloxy-7-(acetyloxymethyl)-3,5,7,8-tetrahydro-2H-[1,4]dithiino[2,3-c]pyridine-6-carboxylate | 1152662-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (7S,8R)-8-acetyloxy-7-(acetyloxymethyl)-3,5,7,8-tetrahydro-2H-[1,4]dithiino[2,3-c]pyridine-6-carboxylate
• CAS: 1152662-17-3
• 化学式: C₁₇H₂₅NO₆S₂
• 分子量: 403.521
• InChiKey: BQCRBQXFMPDRKE-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (7S,8R)-8-acetyloxy-7-(acetyloxymethyl)-3,5,7,8-tetrahydro-2H-[1,4]dithiino[2,3-c]pyridine-6-carboxylate 在 Ra-Ni 作用下， 以 乙醇 为溶剂， 以68%的产率得到tert-butyl (2S,3S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Synthesis of 1-deoxy-l-gulonojirimycin and 1-deoxy-l-talonojirimycin

  摘要：

  De novo synthesis of noncompetitive glycosidase inhibitors L-gulo-DNJ and L-talo-DNJ has been achieved in 9-10 steps starting from Garner's aldehyde. Key to the success of this procedure was the construction of the 2,3-unsaturated piperidine 14, which syn dihydroxylation under Kishi's and Donohoe's conditions led to the desired iminosugars. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.111
• 作为产物：
  描述：

  [(2S,3R)-3-acetyloxy-3-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl] acetate 在 对甲苯磺酰氯 、 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到tert-butyl (7S,8R)-8-acetyloxy-7-(acetyloxymethyl)-3,5,7,8-tetrahydro-2H-[1,4]dithiino[2,3-c]pyridine-6-carboxylate
  参考文献：
  名称：

  Synthesis of 1-deoxy-l-gulonojirimycin and 1-deoxy-l-talonojirimycin

  摘要：

  De novo synthesis of noncompetitive glycosidase inhibitors L-gulo-DNJ and L-talo-DNJ has been achieved in 9-10 steps starting from Garner's aldehyde. Key to the success of this procedure was the construction of the 2,3-unsaturated piperidine 14, which syn dihydroxylation under Kishi's and Donohoe's conditions led to the desired iminosugars. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.111