(R,E)-5-methyl-2-[(triisopropylsilyloxy)methyl]hex-3-enyl carbamic acid tert-butyl ester | 521918-03-6

• 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,E)-5-methyl-2-[(triisopropylsilyloxy)methyl]hex-3-enyl carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(E,2R)-5-methyl-2-[tri(propan-2-yl)silyloxymethyl]hex-3-enyl]carbamate
• CAS: 521918-03-6
• 化学式: C₂₂H₄₅NO₃Si
• 分子量: 399.69
• InChiKey: YMFUDAVIWMSSQP-DRUFCSCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-5-methyl-2-[(triisopropylsilyloxy)methyl]hex-3-enyl carbamic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5R)-5-hydroxymethyl-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetrized tris(hydroxymethyl)methane as precursor of iminosugars: application to the synthesis of isofagomine

  摘要：

  A new synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM*), readily obtained in both enantiomeric forms through a chemoenzymatic procedure, is reported. In this case THYM* precursor 3 was elaborated by ring closing metathesis into some enantiopure branched tetrahydropyridines, that hake been used as precursors of the potent glycosidase inhibitor isofagomine 28. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02492-9
• 作为产物：
  描述：

  (S,E)-2-(methanesulfonyloxy)methyl-5-methylhex-3-enyl acetate 在 咪唑 、 sodium azide 、 Pseudomonas cepacia lipase 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (R,E)-5-methyl-2-[(triisopropylsilyloxy)methyl]hex-3-enyl carbamic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis

  摘要：

  描述了一种新颖的合成应用，即不对称三（羟甲基）甲烷（THYM*）1，采用化学酶法合成获得两种对映异构体，具有较高的对映体富集度。以常见前体3为起始材料，利用环闭合重排作为关键步骤合成了含氮和含氧的六元杂环。探讨了对6和28中双键的可能改造，在28的情况下，成功转化为糖苷酶抑制剂异伐果明53。

  DOI：

  10.1039/b502952j

文献信息

• Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis
  作者：Luca Banfi、Giuseppe Guanti、Monica Paravidino、Renata Riva

  DOI：10.1039/b502952j

  日期：——

  A novel synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM*) 1, obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor 3, N- and O-containing 6-membered heterocycles have been prepared exploiting ring-closing metathesis as the key step. Possible elaborations of the double bond in 6 and 28 have been explored and, in the case of 28, conversion into the glycosidase inhibitor isofagomine 53 has been achieved.

  描述了一种新颖的合成应用，即不对称三（羟甲基）甲烷（THYM*）1，采用化学酶法合成获得两种对映异构体，具有较高的对映体富集度。以常见前体3为起始材料，利用环闭合重排作为关键步骤合成了含氮和含氧的六元杂环。探讨了对6和28中双键的可能改造，在28的情况下，成功转化为糖苷酶抑制剂异伐果明53。
• Asymmetrized tris(hydroxymethyl)methane as precursor of iminosugars: application to the synthesis of isofagomine
  作者：Giuseppe Guanti、Renata Riva

  DOI：10.1016/s0040-4039(02)02492-9

  日期：2003.1

  A new synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM*), readily obtained in both enantiomeric forms through a chemoenzymatic procedure, is reported. In this case THYM* precursor 3 was elaborated by ring closing metathesis into some enantiopure branched tetrahydropyridines, that hake been used as precursors of the potent glycosidase inhibitor isofagomine 28. (C) 2002 Elsevier Science Ltd. All rights reserved.