4-[2-(tert-butyl-dimethyl-silanyloxy)-3-[1,3]dithian-2-yl-3-methyl-butyl]-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane | 335119-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(tert-butyl-dimethyl-silanyloxy)-3-[1,3]dithian-2-yl-3-methyl-butyl]-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane
• 英文别名: tert-butyl-[2-[(4S,6R)-6-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(1,3-dithian-2-yl)-3-methylbutyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethoxy]-diphenylsilane
• CAS: 335119-43-2
• 化学式: C₃₉H₆₄O₄S₂Si₂
• 分子量: 717.238
• InChiKey: MUDIDECXSWPIND-HHMOXRITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.87
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[2-(tert-butyl-dimethyl-silanyloxy)-3-[1,3]dithian-2-yl-3-methyl-butyl]-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane 在 六甲基磷酰三胺 、 四丁基氟化铵 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 49.08h， 生成 2-[6-(2-(tert-butyl-dimethyl-silanyloxy)-3-{2-[4-(2-hydroxy-ethylidene)-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl]-[1,3]dithian-2-yl}-3-methyl-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol
  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：

  7-benzyloxy-8-[1,3]dithian-2-yl-3,5-dihydroxy-8-methyl-nonanoic acid tert-butyl ester 在 对甲苯磺酸 咪唑 、 lithium aluminium tetrahydride 、 LiDBB 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 4-[2-(tert-butyl-dimethyl-silanyloxy)-3-[1,3]dithian-2-yl-3-methyl-butyl]-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane
  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 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.