(E,2S,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-ol | 160836-00-0

• 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: (E,2S,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-ol
• CAS: 160836-00-0
• 化学式: C₂₅H₄₆O₄Si₂
• 分子量: 466.809
• InChiKey: GGEVBRSRTTVDFG-UOGXHXTNSA-N

物化性质

• 沸点：
  482.517±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.962±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,2S,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-ol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 Ethyl (3R,4S,5S)-3-O-acetyl-4,5-bis-O-(tert-butyldimethylsilyl)-8-O-benzyl-3,4,5,8-tetrahydroxy-6E-octenoate
  参考文献：
  名称：

  Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method

  摘要：

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

  DOI：

  10.1021/jo00075a024
• 作为产物：
  描述：

  (E)-3-((4S,5S)-5-((4-ethoxybenzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 在 水 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 (E,2S,3S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-ol
  参考文献：
  名称：

  Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method

  摘要：

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

  DOI：

  10.1021/jo00075a024

文献信息

• Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines
  作者：Seiki Saito、Teruhiko Ishikawa、Toshio Moriwake

  DOI：10.1021/jo00095a008

  日期：1994.8

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.
• Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method
  作者：Seiki Saito、Osamu Narahara、Teruhiko Ishikawa、Masahiro Asahara、Toshio Moriwake、Jacek Gawronski、Franciszek Kazmierczak

  DOI：10.1021/jo00075a024

  日期：1993.11

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.