2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-one | 184174-41-2

• 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-one
• 英文别名: (2R,6S)-2-(hydroxymethyl)-6-(trityloxymethyl)oxan-4-one
• CAS: 184174-41-2
• 化学式: C₂₆H₂₆O₄
• 分子量: 402.49
• InChiKey: GFVJKKFWUQRMLO-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (8R,10S)-3,3-Dimethyl-1,5,9-trioxa-spiro[5.5]undecane-8,10-dicarbaldehyde 在 吡啶 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 sodium tetrahydroborate 、 Lipase PS 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 94.0h， 生成 2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-one
  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

文献信息

• Asymmetric synthesis of the C(10)C(16) segment of the bryostatins
  作者：Thomas F.J. Lampe、H.M.R. Hoffmann

  DOI：10.1016/0040-4039(96)01759-5

  日期：1996.10

  The C(10)C(16) segment of the bryostatins has been synthesized (12 steps, 15 % overall yield) and a cyanohydrin based strategy was developed for coupling with a C(1)C(9) model.

  合成了溴抑他汀的C（10）C（16）片段（12个步骤，总产率15％），并开发了基于氰醇的策略与C（1）C（9）模型耦合。
• Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins
  作者：A. Vakalopoulos、T. F. J. Lampe、H. M. R. Hoffmann

  DOI：10.1021/ol015551o

  日期：2001.3.1

  [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.