(R)-2-<<(Benzyloxy)methoxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>propane | 122535-99-3

• 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: (R)-2-<<(Benzyloxy)methoxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>propane
• 英文别名: (R)-3-benzyloxymethoxy-1-(tert-butyldiphenylsiloxy)-2-methylpropane；tert-butyl-[(2R)-2-methyl-3-(phenylmethoxymethoxy)propoxy]-diphenylsilane
• CAS: 122535-99-3
• 化学式: C₂₈H₃₆O₃Si
• 分子量: 448.678
• InChiKey: KFVWKXXFKZJOCH-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-<<(Benzyloxy)methoxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>propane 在 10 wt% Pd(OH)2 on carbon 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以63%的产率得到(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol
  参考文献：
  名称：

  Preparation of (2 R , 3 R , 4 R )-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization

  摘要：

  Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to, access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.11.050
• 作为产物：
  描述：

  (R)-(E)-2-<<(Benzyloxy)methoxy>methyl>-1-<<(tert-butyldiphenylsilyl)oxy>methyl>non-3-en 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 对甲苯磺酰氯 作用下， 生成 (R)-2-<<(Benzyloxy)methoxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>propane
  参考文献：
  名称：

  在有机合成中作为选择性试剂的酶：“不对称的三（羟甲基）甲烷”的对映选择性制备

  摘要：

  通过PPL催化前手性双乙酸3的单水解，制备了具有优异对映异构性的新的C-4手性结构单元，该结构是三（羟甲基）甲烷衍生物，其中三个等效的羟甲基已被区分[（THYM）* ] 。

  DOI：

  10.1016/s0040-4039(00)99101-9

文献信息

• Enzymes as selective reagents in organic synthesis: Enantioselective preparation of “asymmetrized tris (hydroxymethyl)methane”
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/s0040-4039(00)99101-9

  日期：1989.1

  A new C-4 chiral building block, that is a tris (hydroxymethyl)methane derivative where the three equivalent hydroxymethyl groups have been differentiated [(THYM)*], was prepared with excellent enantioselection, through PPL catalysed monohydrolysis of prochiral diacetate 3.

  通过PPL催化前手性双乙酸3的单水解，制备了具有优异对映异构性的新的C-4手性结构单元，该结构是三（羟甲基）甲烷衍生物，其中三个等效的羟甲基已被区分[（THYM）* ] 。
• GUANTI, GIUSEPPE;BANFI, LUCA;NARISANO, ENRICA, TETRAHEDRON LETT., 30,(1989) N0, C. 2697-2698
  作者：GUANTI, GIUSEPPE、BANFI, LUCA、NARISANO, ENRICA

  DOI：——

  日期：——
• Preparation of (2 R , 3 R , 4 R )-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
  作者：Yoshinori Tokairin、Hiroyuki Konno

  DOI：10.1016/j.tet.2016.11.050

  日期：2017.1

  Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to, access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction. (C) 2016 Elsevier Ltd. All rights reserved.
• 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.