[(2R,3R,5S,6S)-3,5-bis(tert-butyldimethylsilanyloxy)-6-((S)-1-methylallyl)-tetrahydropyran-2-yl]acetic acid methyl ester | 1001061-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,5S,6S)-3,5-bis(tert-butyldimethylsilanyloxy)-6-((S)-1-methylallyl)-tetrahydropyran-2-yl]acetic acid methyl ester
• 英文别名: methyl 2-[(2R,3R,5S,6S)-6-[(2S)-but-3-en-2-yl]-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]oxan-2-yl]acetate
• CAS: 1001061-12-6
• 化学式: C₂₄H₄₈O₅Si₂
• 分子量: 472.813
• InChiKey: LVCQLQUOIOPRPR-MOFJNDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3R,5S,6S)-3,5-bis(tert-butyldimethylsilanyloxy)-6-((S)-1-methylallyl)-tetrahydropyran-2-yl]acetic acid methyl ester 、 9-硼双环[3.3.1]壬烷 以 四氢呋喃 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Highly Functionalized Pyranopyrans from Furans:  A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B

  摘要：

  A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.

  DOI：

  10.1021/ol702559e
• 作为产物：
  描述：

  、 叔丁基二甲硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到[(2R,3R,5S,6S)-3,5-bis(tert-butyldimethylsilanyloxy)-6-((S)-1-methylallyl)-tetrahydropyran-2-yl]acetic acid methyl ester
  参考文献：
  名称：

  Highly Functionalized Pyranopyrans from Furans:  A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B

  摘要：

  A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.

  DOI：

  10.1021/ol702559e

文献信息

• Highly Functionalized Pyranopyrans from Furans:  A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B
  作者：James A. Henderson、Katrina L. Jackson、Andrew J. Phillips

  DOI：10.1021/ol702559e

  日期：2007.12.1

  A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.