(2R,2'S,2''R,3S,4S,6'S,6''S)-3-O-benzyl-1-O,2-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-5-O-pivaloyl-adonitol | 173397-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,2'S,2''R,3S,4S,6'S,6''S)-3-O-benzyl-1-O,2-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-5-O-pivaloyl-adonitol
• CAS: 173397-78-9
• 化学式: C₂₉H₄₄O₈
• 分子量: 520.664
• InChiKey: LIPHDJXDEIPIQM-UFOCRQLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (2R,2'S,2''R,3S,4S,6'S,6''S)-3-O-benzyl-1-O,2-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-5-O-pivaloyl-adonitol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (2R,2'S,2''R,3S,4S,6'S,6''S)-3-O-benzyl-1-O,2-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-4-O-(R)-(α-methoxy-α-(trifluoromethyl)phenylacetyl)-5-O-pivaloyl-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：

  (2R,2'S,2''R,2'''R,2''''S,3S,4S,6'S,6''S,6'''S,6''''S)-3-O-benzyl-1-O,2-O:4-O,5-O-di-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-diyl)-adonitol 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 49.0h， 生成 (2R,2'S,2''R,3S,4S,6'S,6''S)-3-O-benzyl-1-O,2-O-(6,6'-dimethyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-5-O-pivaloyl-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