6(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-4(R)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>-2,2,5(S)-trimethyl-1,3-dioxane | 81470-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-4(R)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>-2,2,5(S)-trimethyl-1,3-dioxane
• 英文别名: 6(R)-{1(R)-methyl-2-[(tert-butyldiphenylsilyl)oxy]ethyl}-4(R)-[1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl]-2,2,5(S)-trimethyl-1,3-dioxane；tert-butyl-diphenyl-[(2R)-2-[(4R,5S,6R)-2,2,5-trimethyl-6-[(1R)-1-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]ethyl]-1,3-dioxan-4-yl]propoxy]silane
• CAS: 81470-91-9
• 化学式: C₃₅H₅₄O₅Si
• 分子量: 582.896
• InChiKey: WOYVFCCPZWTWRU-XAPHVVPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-4(R)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>-2,2,5(S)-trimethyl-1,3-dioxane 在 四丁基氟化铵 作用下， 生成 (R)-2-((4R,5S,6S)-2,2,5-trimethyl-6-((R)-1-((4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethyl)-1,3-dioxan-4-yl)propan-1-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：

  (2R,3R,4S,5S,6R,7S,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4,6,8-tetramethyl-nonane-1,3,7,9-tetraol 在 palladium on activated charcoal 咪唑 、 盐酸 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6(R)-<1(R)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-4(R)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>-2,2,5(S)-trimethyl-1,3-dioxane
  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

文献信息

• Applications of the 3-methyl-.gamma.-butyrolactone strategy to the synthesis of polypropionates: the Prelog-Djerassi lactonic ester, ent-invictolide, and the C19-C27 fragment of rifamycin S
  作者：Frederick E. Ziegler、William T. Cain、Alyssa. Kneisley、Eugene P. Stirchak、Ronald T. Wester

  DOI：10.1021/ja00224a032

  日期：1988.8
• 3-Methyl-γ-butyrolactone as a source of 2-methyl-3-hydroxyketones and 2-methyl-1,3-diols: a synthesis of the C19C27 fragment of rifamycin S by linear iteration
  作者：Frederick E. Ziegler、Alyssa Kneisley

  DOI：10.1016/s0040-4039(00)95405-4

  日期：1987.1
• A highly convergent asymmetric synthesis of the C(19)-C(27) segment of rifamycin S: an application of enantiodifferentiating acetalization with menthone
  作者：Toshiro Harada、Yasuhiro Kagamihara、Sachi Tanaka、Kazuhiko Sakamoto、Akira Oku

  DOI：10.1021/jo00032a004

  日期：1992.3

  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.