(3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2,6-diol | 139016-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2,6-diol
• CAS: 139016-66-3
• 化学式: C₁₃H₂₈O₄Si
• 分子量: 276.448
• InChiKey: HRQCMZMLIXZFDZ-XSQGIZAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2,6-diol 、 alkaline earth salt of/the/ methylsulfuric acid 在 4 A molecular sieve 作用下， 生成 (3R,4R,5S,6S,7R,8S,9S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,5,7,9-tetramethyl-undeca-1,10-diene-4,8-diol 、 (3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((R)-1-methyl-allyl)-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  A highly convergent asymmetric synthesis of the C(19)-C(27) segment of rifamycin S: an application of enantiodifferentiating acetalization with menthone

  摘要：

  An enantiodifferentiating transformation of 1,3-alkanediols by kinetic acetalization with menthone is developed and used in a highly convergent asymmetric synthesis of the C(19)-C(27) segment of the ansa chain of rifamycin S.

  DOI：

  10.1021/jo00032a004
• 作为产物：
  描述：

  meso-(2R,3r,4S)-3-((tert-butyldimethylsilyl)oxy)-2,4-dimethylpentanedial 在 水 作用下， 生成 (3S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2,6-diol
  参考文献：
  名称：

  Reagent Control of Geometric Selectivity and Enantiotopic Group Preference in Asymmetric Horner−Wadsworth−Emmons Reactions with meso-Dialdehydes

  摘要：

  Results from asymmetric Horner-Wadsworth-Emmons reactions between chiral phosphsnate reagents 3a-d, which contain (1R,2S,5R)-8-phenylmenthol as a chiral auxiliary, and meso-dialdehydes 6 and 14 are presented. It was found that both the geometric selectivities and the levels of asymmetric induction depended on the structure of the phosphonate (i.e., the alkyl group R-1 in the phosphoryl unit) and to a certain extent also on the reaction conditions. Furthermore, the nature of the protecting group used on the a-oxygen substituent in dialdehydes 14 influenced the outcome somewhat. By an appropriate choice of reagent and conditions, either (E)- or (Z)-monoaddition products could be obtained geometrically pure and with good to excellent diastereoselectivities, in synthetically useful yields. Analyses of the absolute configurations of the products showed that the (E)-selective reagents (3a-c) and the (Z)-selective phosphonate 3d reacted at opposite enantiotopic carbonyl groups in the substrates. A mechanistic model which accounts for the products formed is presented.

  DOI：

  10.1021/jo981102z