(R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde | 138436-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde
• 英文别名: (2R)-2-[(4-methoxyphenyl)methoxymethoxymethyl]-3-tri(propan-2-yl)silyloxypropanal
• CAS: 138436-32-5
• 化学式: C₂₂H₃₈O₅Si
• 分子量: 410.626
• InChiKey: VQNUBFOAPNEKNS-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde 在 pH 7 phosphate buffer 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-(R)-2-Triisopropylsilanyloxymethyl-hept-3-en-1-ol
  参考文献：
  名称：

  立体发散合成不对称的2-烯基-1,3-丙二醇衍生的顺式环氧化物

  摘要：

  通过不对称的（Z）-2-烯基-1,3-丙二醇的非对映特异性环氧化，以高对映异构和非对映异构的方式获得了任何所需的绝对立体化学的顺式环氧化物，进而通过化学酶促途径和保护-脱保护得到了在羟基上“欺骗”。

  DOI：

  10.1016/s0040-4020(01)80220-9
• 作为产物：
  描述：

  (R)-(E)-5-Methyl-2-<<(triisopropylsilyl)oxy>methyl>hex-3-en-1-ol 在 吡啶 、 二甲基硫 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde
  参考文献：
  名称：

  立体发散合成不对称的2-烯基-1,3-丙二醇衍生的顺式环氧化物

  摘要：

  通过不对称的（Z）-2-烯基-1,3-丙二醇的非对映特异性环氧化，以高对映异构和非对映异构的方式获得了任何所需的绝对立体化学的顺式环氧化物，进而通过化学酶促途径和保护-脱保护得到了在羟基上“欺骗”。

  DOI：

  10.1016/s0040-4020(01)80220-9

文献信息

• Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl)acetaldehydes (BHYMA*)
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/0040-4039(91)80449-g

  日期：1991.11

  MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (hydroxymethyl)acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.
• Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1021/jo00031a039

  日期：1992.2

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.
• Asymmetric synthesis of protected α-alkyl-β-amino-δ-hydroxy esters by stereocontrolled elaboration of THYM*
  作者：Giuseppe Guanti、Alberto Moro、Enrica Narisano

  DOI：10.1016/s0040-4039(00)00351-8

  日期：2000.4

  Highly diastereoselective internal Michael addition of the carbamate moiety of enoate 1b [derived from asymmetrized tris(hydroxymethyl)methane (THYM*)] leads to oxazinone 4, which can, in turn, be alkylated with moderate to good diastereoselectivity in the position cl to the ester moiety to give protected anti,anti alpha-alkyl-beta- amino-delta-hydroxy esters. (C) 2000 Elsevier Science Ltd. All rights reserved.