(2R,2'R,2''R,3R,4S,6'S,6''S)-1-O,5-O-di-(tert-butyldiphenylsilyl)-3-O,4-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-adonitol | 173397-81-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,2'R,2''R,3R,4S,6'S,6''S)-1-O,5-O-di-(tert-butyldiphenylsilyl)-3-O,4-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-adonitol
• CAS: 173397-81-4
• 化学式: C₄₉H₆₆O₇Si₂
• 分子量: 823.23
• InChiKey: GKXALWDWRVOEKQ-ITFWYRRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (2R,2'R,2''R,3R,4S,6'S,6''S)-1-O,5-O-di-(tert-butyldiphenylsilyl)-3-O,4-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-adonitol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (2R,2'R,2''R,3S,4S,6'S,6''S)-1-O,5-O-di-(tert-butyldiphenylsilyl)-3-O,4-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-2-O-((S)-α-methoxy-α-(trifluoromethyl)-phenylacetyl)-adonitol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j
• 作为产物：
  描述：

  <2S,2'S> 2,2'-dimethyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran 、 (2S,3S,4R)-1,5-Bis-(tert-butyl-diphenyl-silanyloxy)-pentane-2,3,4-triol 在 camphor-10-sulfonic acid 作用下， 以 氯仿 为溶剂， 反应 29.0h， 以7%的产率得到(2S,2'R,2''R,3S,4R,6'S,6''S)-1-O,5-O-di-(tert-butyldiphenylsilyl)-3-O,4-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-adonitol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j