((R)-2-Benzyloxy-1-(R)-oxiranyl-ethoxy)-tert-butyl-dimethyl-silane | 326853-47-8

• 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: ((R)-2-Benzyloxy-1-(R)-oxiranyl-ethoxy)-tert-butyl-dimethyl-silane
• 英文别名: tert-butyl-dimethyl-[(1R)-1-[(2R)-oxiran-2-yl]-2-phenylmethoxyethoxy]silane
• CAS: 326853-47-8
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: NVVIGPQSAURLOR-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((R)-2-Benzyloxy-1-(R)-oxiranyl-ethoxy)-tert-butyl-dimethyl-silane 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (1R,6S,7S)-1-[(R)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-7-methoxymethoxy-non-3-ynyl ester
  参考文献：
  名称：

  Formal synthesis of (+)-isolaurepinnacin

  摘要：

  The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the alpha,omega -positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01880-3
• 作为产物：
  描述：

  (4R,5R)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester 在 吡啶 、 Amberlyst 15 、 potassium carbonate 、 silver nitrate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 ((R)-2-Benzyloxy-1-(R)-oxiranyl-ethoxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Formal synthesis of (+)-isolaurepinnacin

  摘要：

  The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the alpha,omega -positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01880-3

文献信息

• Total synthesis of (+)-obtusenyne
  作者：Toshiyuki Uemura、Toshio Suzuki、Naohiro Onodera、Hisahiro Hagiwara、Takashi Hoshi

  DOI：10.1016/j.tetlet.2006.11.080

  日期：2007.1

  The stercoselective total synthesis of (+)-obtusenyne is described. The oxonene skeleton possessing trans-orientated alkyl substituents at the alpha,alpha'-positions was stereoselectively constructed via cyclization of the corresponding hydroxy epoxide promoted by Eu(fod)(3). (c) 2006 Published by Elsevier Ltd.
• Formal synthesis of (+)-isolaurepinnacin
  作者：Toshio Suzuki、Ryuji Matsumura、Ken-ichi Oku、Keiichi Taguchi、Hisahiro Hagiwara、Takashi Hoshi、Masayoshi Ando

  DOI：10.1016/s0040-4039(00)01880-3

  日期：2001.1

  The stereoselective formal synthesis of (+)-isolaurepinnacin is described. The required key oxepene skeleton possessing cis-oriented alkyl substituents at the alpha,omega -positions was stereoselectively constructed via the cyclization of the corresponding hydroxy epoxide promoted by the (Bu3Sn)(2)O/Zn(OTf)(2) system. (C) 2000 Elsevier Science Ltd. All rights reserved.