(2R,4S,6S)-(6-allyl-4-triisopropylsilyloxy-tetrahydropyran-2-yl)-acetic acid methyl ester | 222172-12-5

• 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: (2R,4S,6S)-(6-allyl-4-triisopropylsilyloxy-tetrahydropyran-2-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(2R,4S,6S)-6-prop-2-enyl-4-tri(propan-2-yl)silyloxyoxan-2-yl]acetate
• CAS: 222172-12-5
• 化学式: C₂₀H₃₈O₄Si
• 分子量: 370.605
• InChiKey: RMHRWZUDLJQRKG-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S,6S)-(6-allyl-4-triisopropylsilyloxy-tetrahydropyran-2-yl)-acetic acid methyl ester 在 咪唑 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.25h， 生成 2-{(2S,4R,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-ethanol
  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 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.0h， 生成 (2R,4S,6S)-(6-allyl-4-triisopropylsilyloxy-tetrahydropyran-2-yl)-acetic acid methyl ester
  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.