(2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal | 138436-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal
• CAS: 138436-30-3
• 化学式: C₂₉H₃₆O₅Si
• 分子量: 492.687
• InChiKey: MTSRUANVYIIYLX-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal 在 pH 7 buffer 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,5R)-trans-4-allyl-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxane
  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
• 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 (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]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

• Synthesis of a key intermediate for Thienamycin and Imipenem through stereoselective two-direction elongation of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA∗)
  作者：Luca Banfi、Giuseppe Guanti、Maria Teresa Zannetti

  DOI：10.1016/0040-4039(95)02177-9

  日期：1996.1

  The enantioselective formal synthesis of Thienamycin and Imipenem has been realised through two-direction elongation of the chiral building block bis(hydroxymethyl)acetaldehyde 5. The generation of the two additional stereocentres has been carried out with excellent diastereoselectivity thanks to two sequential “protecting group controlled” nucleophilic additions. Another key step was represented by

  通过手性结构单元双（羟甲基）乙醛5的双向延伸，实现了噻菌霉素和亚胺培南的对映体选择性形式合成。由于两个连续的“受保护基团控制的”亲核加成，两个额外的立体中心的生成具有出色的非对映选择性。另一个关键步骤以伯-仲1,3-二醇区域选择性氧化为相应的β-羟酸为代表。
• 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.