(E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester | 149525-94-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (E,4R,6R,8S)-4,8-bis[[tert-butyl(diphenyl)silyl]oxy]-9-oxo-6-phenylmethoxynon-2-enoate
• CAS: 149525-94-0
• 化学式: C₆₄H₇₈O₆Si₂
• 分子量: 999.491
• InChiKey: KJWPBABKWQWDLR-AAQFWGFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.32
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 在 吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 作用下， 生成 (E)-3-[(2R,4R,6R)-4-benzyloxy-6-hydroxymethyltetrahydropyran-2-yl]acrylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
  参考文献：
  名称：

  Asymmetric Horner-Wadsworth-Emmons Reactions with Meso-Dialdehydes: Scope, Mechanism, and Synthetic Applications

  摘要：

  DOI：

  10.1080/10426509908546209
• 作为产物：
  描述：

  6-(benzyloxy)-1,3-cycloheptadiene 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
  参考文献：
  名称：

  Asymmetric Horner-Wadsworth-Emmons reactions using meso dialdehydes as substrates

  摘要：

  Asymmetric Horner-Wadsworth-Emmons reactions of the chiral phosphonate 7 with meso dialdehydes 1 and 4 gave the desired monoaddition products with good diastereoselectivities (87:13-97:3) and high (E)-selectivity.

  DOI：

  10.1021/jo00067a010

文献信息

• Reagent Control of Geometric Selectivity and Enantiotopic Group Preference in Asymmetric Horner−Wadsworth−Emmons Reactions with <i>meso</i>-Dialdehydes
  作者：Joshua S. Tullis、Lauri Vares、Nina Kann、Per-Ola Norrby、Tobias Rein

  DOI：10.1021/jo981102z

  日期：1998.11.1

  Results from asymmetric Horner-Wadsworth-Emmons reactions between chiral phosphsnate reagents 3a-d, which contain (1R,2S,5R)-8-phenylmenthol as a chiral auxiliary, and meso-dialdehydes 6 and 14 are presented. It was found that both the geometric selectivities and the levels of asymmetric induction depended on the structure of the phosphonate (i.e., the alkyl group R-1 in the phosphoryl unit) and to a certain extent also on the reaction conditions. Furthermore, the nature of the protecting group used on the a-oxygen substituent in dialdehydes 14 influenced the outcome somewhat. By an appropriate choice of reagent and conditions, either (E)- or (Z)-monoaddition products could be obtained geometrically pure and with good to excellent diastereoselectivities, in synthetically useful yields. Analyses of the absolute configurations of the products showed that the (E)-selective reagents (3a-c) and the (Z)-selective phosphonate 3d reacted at opposite enantiotopic carbonyl groups in the substrates. A mechanistic model which accounts for the products formed is presented.
• Asymmetric Horner-Wadsworth-Emmons reactions using meso dialdehydes as substrates
  作者：Nina Kann、Tobias Rein

  DOI：10.1021/jo00067a010

  日期：1993.7

  Asymmetric Horner-Wadsworth-Emmons reactions of the chiral phosphonate 7 with meso dialdehydes 1 and 4 gave the desired monoaddition products with good diastereoselectivities (87:13-97:3) and high (E)-selectivity.
• Asymmetric Horner-Wadsworth-Emmons Reactions with <i>Meso</i>-Dialdehydes: Scope, Mechanism, and Synthetic Applications
  作者：Tobias Rein、Lauri Vares、Ikuo Kawasaki、Torben M. Pedersen、Per-Ola Norrby、Peter Brandt、David Tanner

  DOI：10.1080/10426509908546209

  日期：1999.1.1