tert-butyl (2S,4R,6R)-{4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]-2-hydroxytetrahydropyran-2-yl}acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: tert-butyl (2S,4R,6R)-{4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]-2-hydroxytetrahydropyran-2-yl}acetate
• 英文别名: tert-butyl 2-[(2S,4R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[2-(1,3-dithian-2-yl)propan-2-yl]-2-hydroxyoxan-2-yl]acetate
• 化学式: C₂₄H₄₆O₅S₂Si
• 分子量: 506.844
• InChiKey: UMWFXRXPKYXSCY-GGUMNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl (2S,4R,6R)-{4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]-2-hydroxytetrahydropyran-2-yl}acetate 在 柠檬酸 作用下， 反应 6.0h， 以81%的产率得到tert-butyl (2S,4R,6R)-{4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]-2-methoxytetrahydropyran-2-yl}acetate
  参考文献：
  名称：

  Structural and Stereochemical Diversity from (±)-2,2-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one − Application to the Synthesis of Polyketide Segments of Natural Products

  摘要：

  The racemic title compound has been transformed into both Cyclic and acyclic segments of bioactive natural products, including the C10-C17 segment of pederin, the C12-C19 (C12'-C19') segment of disorazole and the C1-C9 segment of auriside. A methodology for the opening of six-membered ring acetals, containing gem-dimethyl groups, to 5-hydroxyl,3-dithianes has been developed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200205)2002:9<1538::aid-ejoc1538>3.0.co;2-x
• 作为产物：
  描述：

  (4R,6R)-6-{1-[(1,3-dithian-2-yl)-1-methylethyl]}-4-hydroxytetrahydropyran-2-one 在 咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl (2S,4R,6R)-{4-(tert-butyldimethylsilanyloxy)-6-[1-(1,3-dithian-2-yl)-1-methylethyl]-2-hydroxytetrahydropyran-2-yl}acetate
  参考文献：
  名称：

  Structural and Stereochemical Diversity from (±)-2,2-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one − Application to the Synthesis of Polyketide Segments of Natural Products

  摘要：

  The racemic title compound has been transformed into both Cyclic and acyclic segments of bioactive natural products, including the C10-C17 segment of pederin, the C12-C19 (C12'-C19') segment of disorazole and the C1-C9 segment of auriside. A methodology for the opening of six-membered ring acetals, containing gem-dimethyl groups, to 5-hydroxyl,3-dithianes has been developed.((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200205)2002:9<1538::aid-ejoc1538>3.0.co;2-x