| 134221-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 134221-97-9
• 化学式: C₂₇H₄₄O₈Si
• 分子量: 524.727
• InChiKey: BXEGWWQQMPINLV-BECHRVIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到
  参考文献：
  名称：

  Diastereoselective reduction of α-keto esters bearing chiro-inositol derivatives as chiral auxiliaries

  摘要：

  The reduction of alpha-keto esters derived from (1L)-1,2;5, 6-biscyclohexylidene-3-tert-butyldimethysilyl-chiro-inositol with Selectride(R) proceeded with high diastereoselectivity to afford the corresponding alpha-hydroxy esters. Addition of 18-Crown-6 led to dramatic changeover in diastereofacial selectivity.

  DOI：

  10.1016/s0040-4039(00)79661-4
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 dipyriyl disulfide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Diastereoselective reduction of α-keto esters bearing chiro-inositol derivatives as chiral auxiliaries

  摘要：

  The reduction of alpha-keto esters derived from (1L)-1,2;5, 6-biscyclohexylidene-3-tert-butyldimethysilyl-chiro-inositol with Selectride(R) proceeded with high diastereoselectivity to afford the corresponding alpha-hydroxy esters. Addition of 18-Crown-6 led to dramatic changeover in diastereofacial selectivity.

  DOI：

  10.1016/s0040-4039(00)79661-4

文献信息

• Asymmetric synthesis of tetrahydrofurans by diastereoselective [3+2] cycloaddition of allylsilanes with α-keto esters bearing an optically active cyclitol as a chiral auxiliary
  作者：Takahiko Akiyama、Takuya Yasusa、Keiichiro Ishikawa、Shoichiro Ozaki

  DOI：10.1016/s0040-4039(00)74417-0

  日期：1994.11

  Tin (IV) chloride mediated [3+2] cycloadditions of allylsilanes with optically active α-keto esters derived from L-quebrachitol afforded tetrahydrofuran derivatives via 1,2-silyl migration with high level of diastereoselectivity. Removal of the chiral auxiliary gave silyl-substituted tetrahydrofurans of excellent optical purity.

  氯化锡（IV）介导的烯丙基硅烷与衍生自L-邻苯二酚的光学活性α-酮酯的[3 + 2]环加成反应通过1,2-甲硅烷基迁移以高非对映选择性提供四氢呋喃衍生物。除去手性助剂得到具有优异光学纯度的甲硅烷基取代的四氢呋喃。
• Diastereoselective Addition of Organometallics to α-Keto Esters Bearing<i>chiro</i>-Inositol Derivatives as Chiral Auxiliaries
  作者：Takahiko Akiyama、Hiroyuki Nishimoto、Keiichiro Ishikawa、Shoichiro Ozaki

  DOI：10.1246/cl.1992.447

  日期：1992.3

  The nucleophilic addition of organometallics to α-keto esters derived from (1L)-1,2:5,6-di-O-cyclohexylidene-3-t-butyldimethylsilyl-chiro-inositol afforded the corresponding α-hydroxy esters of high diastereomeric excess (up to 98% de). Grignard reagents attacked from re-face, while organolithium reagents preferred si-face attack.

  有机金属化合物与衍生自 (1L)-1,2:5,6-di-O-cyclohexylidene-3-t-butyldimethylsilyl-chiro-inositol 的 α-酮酯的亲核加成得到相应的高非对映体过量的 α-羟基酯（高达 98% de）。格氏试剂从 re-face 攻击，而有机锂试剂更喜欢 si-face 攻击。