4-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-oxobutanal | 330970-44-0

• 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: 4-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-oxobutanal
• CAS: 330970-44-0
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: TZJSSOYFAVXJCD-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-oxobutanal 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， -78.0~20.0 ℃ 、551.58 kPa 条件下， 反应 36.0h， 生成 (6S,7R,8R,8aS)-6,7,8-trihydroxy-indolizidine
  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：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 草酰氯 、 magnesium 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-oxobutanal
  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

文献信息

• A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine
  作者：Nitin T Patil、Jayant N Tilekar、Dilip D Dhavale

  DOI：10.1016/s0040-4039(00)02103-1

  日期：2001.1

  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.