(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethoxy)propanal | 133377-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethoxy)propanal
• CAS: 133377-92-1
• 化学式: C₁₈H₃₀O₄Si
• 分子量: 338.519
• InChiKey: SFXYXSTZGQULLA-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethoxy)propanal 在 sodium tetrahydroborate 作用下， 生成 (R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol
  参考文献：
  名称：

  Enzymes in organic synthesis: remarkable influence of a π system on the enantioselectivity in PPL catalysed monohydrolysis of 2-substituted 1,3-diacetoxypropanes.

  摘要：

  DOI：

  10.1016/s0957-4166(00)82383-6
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 甲醇 、 氢氧化钾 、 二甲基硫 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(phenylmethoxymethoxy)propanal
  参考文献：
  名称：

  Asymmetrized trils (hydroxymethyl)methane as a highly stereodivergent chiral building block: preparation of all four stereoisomers of protected 2-hydroxymethyl-1,3-butanediol

  摘要：

  DOI：

  10.1016/s0040-4039(00)97081-3

文献信息

• Enantiospecific and diastereoselective synthesis of C11-C17 fragment of tylonolide from “asymmetrized tris (hydroxymethyl)methane”
  作者：Giuseppe Guanti、Luca Banfi、Chiara Ghiron、Enrica Narisano

  DOI：10.1016/0040-4039(91)80872-4

  日期：1991.1

  The fragment C11-C17 of tylonolide 2 was straightforwardly and stereoselectively synthesized starting from monoacetate 5, which is a synthetic equivalent of “asymmetrized tris (hydroxymethyl)methane” 3.

  从单乙酸酯5开始直接合成和立体选择性地合成了泰诺醇化物2的片段C 11 -C 17，单乙酸酯5是“不对称的三（羟甲基）甲烷” 3的合成等价物。
• 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.