(2S,4S,6S)-6-allyl-2-(2-tert.-butyldimethylsilyloxy-ethyl)-4-triisopropylsilyloxy-tetrahydropyran | 222172-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,4S,6S)-6-allyl-2-(2-tert.-butyldimethylsilyloxy-ethyl)-4-triisopropylsilyloxy-tetrahydropyran
• CAS: 222172-15-8
• 化学式: C₂₅H₅₂O₃Si₂
• 分子量: 456.857
• InChiKey: TYYWZNPIASQXLR-HJOGWXRNSA-N

物化性质

• 沸点：
  443.470±30.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.899±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,6S)-6-allyl-2-(2-tert.-butyldimethylsilyloxy-ethyl)-4-triisopropylsilyloxy-tetrahydropyran 在 臭氧 、 三苯基膦 、 (-)-B-methoxydiisopinocampheylborane 作用下， 反应 7.0h， 生成 (2R)-1-<(2S,4R,6S)-6-(2-tert.-butyldimethylsilyloxy-ethyl)-4-triisopropylsilyloxy-tetrahydropyran-2-yl>-pent-4-en-2-ol
  参考文献：
  名称：

  trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B

  摘要：

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01196-x
• 作为产物：
  描述：

  <(2R,4R)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 (2S,4S,6S)-6-allyl-2-(2-tert.-butyldimethylsilyloxy-ethyl)-4-triisopropylsilyloxy-tetrahydropyran
  参考文献：
  名称：

  trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B

  摘要：

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01196-x

文献信息

• trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B
  作者：Peter Wolbers、H Martin、R Hoffmann

  DOI：10.1016/s0040-4020(98)01196-x

  日期：1999.2

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.