(2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-acetic acid isopropyl ester | 335119-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-acetic acid isopropyl ester
• 英文别名: propan-2-yl (2E)-2-[(2R,6S)-2-(hydroxymethyl)-6-(trityloxymethyl)oxan-4-ylidene]acetate
• CAS: 335119-97-6
• 化学式: C₃₁H₃₄O₅
• 分子量: 486.608
• InChiKey: IOFHXTGYKVQMKD-RJOREIDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-acetic acid isopropyl ester 在 咪唑 、 二异丁基氢化铝 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethylidene]-2-triisopropylsilanyloxymethyl-6-trityloxymethyl-tetrahydropyran
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o
• 作为产物：
  描述：

  diisopropyl ester of isopropoxycarbonylmethylphosphonic acid 、 2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-one 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以99%的产率得到(2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-ylidene)-acetic acid isopropyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o