(R)-3-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-propanal | 138436-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-propanal
• 英文别名: (2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal
• CAS: 138436-28-9
• 化学式: C₁₉H₃₂O₅Si
• 分子量: 368.546
• InChiKey: BQIMVWWINUUZFS-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-propanal 在 2,6-二甲基吡啶 、 copper(l) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 4.67h， 生成 (2R,3R)-1-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butane
  参考文献：
  名称：

  化学酶法制备碳青霉烯的关键中间体，从不对称的双（羟甲基）乙醛（BHYMA *）开始

  摘要：

  从合成的不对称双（羟甲基）乙醛（BHYMA *）4对映体和非对映选择性地制备了4-非取代的2-氮杂环丁酮3a，b，它们是合成碳青霉烯抗生素的有用中间体，是一种通过生物方法获得的新手性结构单元。关键步骤是将Me 2 CuLi高度非对映选择性地添加到4中（最小比率= 95：5），以及在存在（t Pr）3 Si醚的情况下，通过使用a进行t BuMe 2 Si醚的区域选择性解封闭。新颖的方法。

  DOI：

  10.1016/s0040-4020(01)87214-8
• 作为产物：
  描述：

  1-[(氯甲氧基)甲基]-4-甲氧基苯 在 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)-3-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-propanal
  参考文献：
  名称：

  Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  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.

  DOI：

  10.1016/0040-4039(91)80449-g

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.
• Chemoenzymatic preparation of a key intermediate for carbapenem synthesis starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*)
  作者：Luca Banfi、Giuseppe Guanti、Enrica Narisano

  DOI：10.1016/s0040-4020(01)87214-8

  日期：1993.8

  4-Unsubstituted 2-azetidinones 3a,b, which are useful intermediates for the synthesis of carbapenem antibiotics, have been enantiospecifically and diastereoselectively prepared starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*)4, a new chiral building block obtained through biological methods. The key steps are the highly diastereoselective addition of Me2CuLi to 4 (diast. ratio = 95

  从合成的不对称双（羟甲基）乙醛（BHYMA *）4对映体和非对映选择性地制备了4-非取代的2-氮杂环丁酮3a，b，它们是合成碳青霉烯抗生素的有用中间体，是一种通过生物方法获得的新手性结构单元。关键步骤是将Me 2 CuLi高度非对映选择性地添加到4中（最小比率= 95：5），以及在存在（t Pr）3 Si醚的情况下，通过使用a进行t BuMe 2 Si醚的区域选择性解封闭。新颖的方法。