(2S,4R)-[4-(tert-butyldimethylsilyloxy)-2-benzyloxymethyl]cyclopentan-1-one-1,3-propanedithioketal | 1169647-70-4

• 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,4R)-[4-(tert-butyldimethylsilyloxy)-2-benzyloxymethyl]cyclopentan-1-one-1,3-propanedithioketal
• 英文别名: tert-butyl-dimethyl-[[(2R,4S)-4-(phenylmethoxymethyl)-6,10-dithiaspiro[4.5]decan-2-yl]oxy]silane
• CAS: 1169647-70-4
• 化学式: C₂₂H₃₆O₂S₂Si
• 分子量: 424.744
• InChiKey: IJNXVDXMEZICBH-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-[4-(tert-butyldimethylsilyloxy)-2-benzyloxymethyl]cyclopentan-1-one-1,3-propanedithioketal 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以28%的产率得到(2S,4R)-[4-(tert-butyldimethylsilyloxy)-2-(benzyloxymethyl)]cyclopentanone
  参考文献：
  名称：

  An enantioselective synthesis of carbafuranose sugars based on a linchpin carbacyclisation approach

  摘要：

  Enantiopure carbafuranose derivatives were synthesised via a linchpin carbacyclisation process starting from 1,4-bisepoxides. Both 2-deoxy and 2-deoxy-6-hydroxycarbafuranose derivatives were obtained, which were converted to suitably protected precursors for carbanucleoside synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.019
• 作为产物：
  描述：

  (1R,3S)-[3-(tert-butyldimethylsilanyloxy)-6,10-dithiaspiro[4,5]dec-1-yl]-methanol 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 17.0h， 以52%的产率得到(2S,4R)-[4-(tert-butyldimethylsilyloxy)-2-benzyloxymethyl]cyclopentan-1-one-1,3-propanedithioketal
  参考文献：
  名称：

  An enantioselective synthesis of carbafuranose sugars based on a linchpin carbacyclisation approach

  摘要：

  Enantiopure carbafuranose derivatives were synthesised via a linchpin carbacyclisation process starting from 1,4-bisepoxides. Both 2-deoxy and 2-deoxy-6-hydroxycarbafuranose derivatives were obtained, which were converted to suitably protected precursors for carbanucleoside synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.019

文献信息

• An enantioselective synthesis of carbafuranose sugars based on a linchpin carbacyclisation approach
  作者：Leo M.H. Leung、Mark E. Light、Vicky Gibson、Bruno Linclau

  DOI：10.1016/j.tetasy.2009.02.019

  日期：2009.5

  Enantiopure carbafuranose derivatives were synthesised via a linchpin carbacyclisation process starting from 1,4-bisepoxides. Both 2-deoxy and 2-deoxy-6-hydroxycarbafuranose derivatives were obtained, which were converted to suitably protected precursors for carbanucleoside synthesis. (C) 2009 Elsevier Ltd. All rights reserved.