(2S,3S)-2-(Benzyloxymethoxy)-3-(benzyloxymethyl)butane-1,4-diyl dimethanesulfonate | 853270-47-0

• 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: (2S,3S)-2-(Benzyloxymethoxy)-3-(benzyloxymethyl)butane-1,4-diyl dimethanesulfonate
• 英文别名: [(2S,3S)-4-methylsulfonyloxy-3-(phenylmethoxymethoxy)-2-(phenylmethoxymethyl)butyl] methanesulfonate
• CAS: 853270-47-0
• 化学式: C₂₂H₃₀O₉S₂
• 分子量: 502.607
• InChiKey: ILUKYWQXLRTRKD-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(Benzyloxymethoxy)-3-(benzyloxymethyl)butane-1,4-diyl dimethanesulfonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、482.63 kPa 条件下， 反应 112.0h， 生成 cis-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride
  参考文献：
  名称：

  An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate

  摘要：

  A concise stereoselective synthesis of an imino sugar, (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate has been developed in five steps and in overall yield of 28%. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.03.077
• 作为产物：
  描述：

  diethyl (2S,3R)-3-benzoyloxymethyl-2-benzyloxymethoxysuccinate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 (2S,3S)-2-(Benzyloxymethoxy)-3-(benzyloxymethyl)butane-1,4-diyl dimethanesulfonate
  参考文献：
  名称：

  An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate

  摘要：

  A concise stereoselective synthesis of an imino sugar, (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate has been developed in five steps and in overall yield of 28%. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.03.077

文献信息

• Process for the preparation of substituted pyrrolidine derivatives and intermediates
  申请人：Chand Pooran

  公开号：US20060128789A1

  公开（公告）日：2006-06-15

  Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.

  提供两种合成方法；一种是制备(3R,4R)-4-(羟甲基)吡咯烷-3-醇，另一种是制备(3S,4R)-4-(羟甲基)吡咯烷-3-醇。使用从苄胺而非苯乙胺制备的无手性叶烯制备(3R,4R)-4-(羟甲基)吡咯烷-3-醇（方案3），该方法提供了结晶中间体。根据方案4的描述，可以从(S)-乙二酸二乙酯合成(3S,4R)-4-(羟甲基)吡咯烷-3-醇。还提供了一种制备樟脑磺酰胺的方法。
• US7230119B2
  申请人：——

  公开号：US7230119B2

  公开（公告）日：2007-06-12
• An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate
  作者：Pravin L. Kotian、Pooran Chand

  DOI：10.1016/j.tetlet.2005.03.077

  日期：2005.5

  A concise stereoselective synthesis of an imino sugar, (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate has been developed in five steps and in overall yield of 28%. (c) 2005 Published by Elsevier Ltd.