(6Z,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-6-en-2-yn-4-ol | 444885-16-9

• 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: (6Z,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-6-en-2-yn-4-ol
• 英文别名: (Z,9S)-9-[tert-butyl(dimethyl)silyl]oxy-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethoxynon-6-en-2-yn-4-ol
• CAS: 444885-16-9
• 化学式: C₂₇H₄₂O₅Si
• 分子量: 474.713
• InChiKey: PDGRZOHIAPTHJW-JEHMYCOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6Z,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-6-en-2-yn-4-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(1S,3Z)-9-benzyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-3-en-7-yne-1,6-diol
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7
• 作为产物：
  描述：

  (2RS,7S)-7-(tert-butyldimethyl-silanyloxy)-7-[(4R)-2,2-dimethyl-1,3-dioxalan-4-yl]-4-heptene-1,2-diol 在 sodium periodate 、 正丁基锂 、 四丁基高碘酸铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.0h， 生成 (6Z,9S)-1-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-9-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-6-en-2-yn-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7

文献信息

• Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes
  作者：David D Dı́az、Juan M Betancort、Fernando R.P Crisóstomo、Tomás Martı́n、Vı́ctor S Martı́n

  DOI：10.1016/s0040-4020(02)00046-7

  日期：2002.3

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.