(3R,4S,4aR,5S,7aS)-3-hydroxymethyl-1,3,4a,5,7a-hexahydro-5-methoxy-4-phenylmethoxy-cyclopenta[c]pyran-7-methanol | 387867-05-2

• 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: (3R,4S,4aR,5S,7aS)-3-hydroxymethyl-1,3,4a,5,7a-hexahydro-5-methoxy-4-phenylmethoxy-cyclopenta[c]pyran-7-methanol
• 英文别名: (3R,4S,4aS,5S,7aS)-7-(hydroxymethyl)-5-methoxy-3-(phenylmethoxymethyl)-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-4-ol
• CAS: 387867-05-2
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: XCYBIJDHOMXSDI-CWQOZTLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3R,4S,4aR,5S,7aS)-3-hydroxymethyl-1,3,4a,5,7a-hexahydro-5-methoxy-4-phenylmethoxy-cyclopenta[c]pyran-7-methanol 在 吡啶 作用下， 以90%的产率得到(3R,4S,4aR,5S,7aS)-4-acetyloxy-(3-phenylmethoxy)methyl-1,3,4,4a,5,7a-hexahydro-5-methoxy-cyclopenta[c]pyran-7-methanol acetate
  参考文献：
  名称：

  DIBALH mediated reduction of the acetal moiety on perhydrofuro[2,3-b]pyran derivatives

  摘要：

  The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built on these substrates remain practically or partially unaltered in these conditions depending on the steric volume of the O-protecting group located at C-4 (TBDMS vs. Me). This protocol can be considered as a new entry for the synthesis of chiral and highly functionalized cyclopentanes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00200-2
• 作为产物：
  描述：

  (1S,4aS,5aR,8S,9aS,9bR,9cS)-8-Phenyl-1,3,4a,5a,6,9a,9b,9c-octahydro-4,5,7,9-tetraoxa-pentaleno[1,6-ab]naphthalen-1-ol 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (3R,4S,4aR,5S,7aS)-3-hydroxymethyl-1,3,4a,5,7a-hexahydro-5-methoxy-4-phenylmethoxy-cyclopenta[c]pyran-7-methanol
  参考文献：
  名称：

  DIBALH mediated reduction of the acetal moiety on perhydrofuro[2,3-b]pyran derivatives

  摘要：

  The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built on these substrates remain practically or partially unaltered in these conditions depending on the steric volume of the O-protecting group located at C-4 (TBDMS vs. Me). This protocol can be considered as a new entry for the synthesis of chiral and highly functionalized cyclopentanes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00200-2