(2R,3S,4S)-[3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(trityloxymethyl)]cyclopentanone | 1169647-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4S)-[3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(trityloxymethyl)]cyclopentanone
• CAS: 1169647-76-0
• 化学式: C₃₈H₄₄O₄Si
• 分子量: 592.85
• InChiKey: RNSAQJLDDIMWHX-QBDOPFNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-[3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(trityloxymethyl)]cyclopentanone 在 sodium cyanoborohydride 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到(1S,2S,3S,4S)-[3-benzyloxy-4-(tertbutyldimethylsilyloxy)-2-(trityloxymethyl)]cyclopentanol
  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：

  (2S,3S,4R)-(3-benzyloxy-4-trityloxymethyl-6,10-dithiaspiro[4.5]dec-2-yloxy)-tert-butyldimethylsilane 在 N-溴代丁二酰亚胺(NBS) 、 lithium perchlorate 、 silver nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以41%的产率得到(2R,3S,4S)-[3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(trityloxymethyl)]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