(2R,3R,4S)-[3-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl]cyclopentanone | 1169647-74-8

• 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: (2R,3R,4S)-[3-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl]cyclopentanone
• 英文别名: (2R,3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-3-phenylmethoxycyclopentan-1-one
• CAS: 1169647-74-8
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: JJSZLHMGAZJMGN-RYQLBKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-[3-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl]cyclopentanone 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(1R,2S,3R,4S)-[3-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl]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：

  (1R,2R,3S)-[2-benzyloxy-3-(tert-butyldimethylsilanyloxy)-6,10-dithiaspiro[4,5]dec-1-yl]-methanol 在 N-溴代丁二酰亚胺(NBS) 、 lithium perchlorate 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到(2R,3R,4S)-[3-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-hydroxymethyl]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

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.