1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-[1,3]dioxolan-2-yl-propan-1-ol | 330970-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-[1,3]dioxolan-2-yl-propan-1-ol
• CAS: 330970-46-2
• 化学式: C₂₀H₂₈O₇
• 分子量: 380.438
• InChiKey: KZRBOUDRMWRNEF-MSEHENTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-[1,3]dioxolan-2-yl-propan-1-ol 在 草酰氯 、 sodium cyanoborohydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， -78.0~70.0 ℃ 、551.58 kPa 条件下， 反应 42.0h， 生成 (S)-2-((2R,3R,4R,5S)-3,4,5-Trihydroxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

  摘要：

  A new route for the synthesis of 1-deoxy-castanospermine 2 and 1-deoxy-8a-epi-castanospermine 3 has been developed via a sequential triple reductive amination process of a suitably protected D-gluco-oct-5-ulo-1,8-dialdose, which was easily prepared by three carbon homologation of readily available alpha -D-xylo-pentodialdose using an appropriate Grignard reagent followed by oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02103-1
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 magnesium 作用下， 以 乙醚 为溶剂， 以90%的产率得到1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-[1,3]dioxolan-2-yl-propan-1-ol
  参考文献：
  名称：

  A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

  摘要：

  A new route for the synthesis of 1-deoxy-castanospermine 2 and 1-deoxy-8a-epi-castanospermine 3 has been developed via a sequential triple reductive amination process of a suitably protected D-gluco-oct-5-ulo-1,8-dialdose, which was easily prepared by three carbon homologation of readily available alpha -D-xylo-pentodialdose using an appropriate Grignard reagent followed by oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02103-1