(2S,3R)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol | 164907-50-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol
• 英文别名: [(2S,3R)-3-[3-[tert-butyl(diphenyl)silyl]oxypropyl]oxiran-2-yl]methanol
• CAS: 164907-50-0
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: BQVGEAMUMPAUCW-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol 在 pyridine-SO3 complex 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S,4S,5R)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate
  参考文献：
  名称：

  Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes

  摘要：

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00844-3
• 作为产物：
  描述：

  tert-butyl-pent-4-ynyloxy-diphenyl-silane 在 palladium on activated charcoal 、 Pd-BaSO₄ titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 L-(+)-酒石酸二乙酯 、 氢气 作用下， 以 喹啉 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (2S,3R)-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)-2-oxiranyl)methan-1-ol
  参考文献：
  名称：

  Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes

  摘要：

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00844-3

文献信息

• Total synthesis of balanol, part 1. Enantioselective synthesis of the hexahydroazepine ring via chiral epoxides and aziridines
  作者：David Tanner、Antonio Almario、Thomas Högberg

  DOI：10.1016/0040-4020(95)00264-9

  日期：1995.5

  Three different routes to the hexahydroazepine unit of the natural products balanol (1) and ophiocordin (2) are described. The common starting material is the chiral epoxy alcohol 3 which is converted to the balanol degradation product 10 (Scheme 1) or to suitably protected derivatives thereof: 15 (Scheme 2) and 19 (Scheme 3). A key step in the first route is the acid-catalysed ring-opening of bicyclic

  描述了三种不同的天然产物Balanol（1）和ophiocordin（2）通往六氢氮杂unit单元的途径。常见的起始原料是手性环氧醇3，其被转化为Balanol降解产物10（方案1）或其适当保护的衍生物：15（方案2）和19（方案3）。第一条途径中的关键步骤是双环氮丙啶8的酸催化开环，其化学收率高（分离出71％），并且具有显着的区域选择性（98：2有利于所需的区域异构体）。
• ALVAREZ, ELEUTERIO;NUNEZ, MARIA TERESA;MARTIN, VICTOR S., J. ORG. CHEM., 55,(1990) N1, C. 3429-3431
  作者：ALVAREZ, ELEUTERIO、NUNEZ, MARIA TERESA、MARTIN, VICTOR S.

  DOI：——

  日期：——
• Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes
  作者：Kassoum Nacro、Michel Baltas、Liliane Gorrichon

  DOI：10.1016/s0040-4020(99)00844-3

  日期：1999.12

  Aldol condensations on alpha-,beta-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and sny gamma,delta-epoxy beta-hydroxyesters and their NMR and IR spectrostroscopic properties. (C) 1999 Elsevier Science Ltd. All rights reserved.