(2R)-2-tert-butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoic acid methyl ester | 890049-74-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-2-tert-butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoic acid methyl ester
• 英文别名: methyl (E,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-trimethylsilylpent-3-enoate
• CAS: 890049-74-8
• 化学式: C₁₄H₂₇NO₄Si
• 分子量: 301.458
• InChiKey: RTKRYTYRRBSDPI-ANYFNZRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-tert-butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoic acid methyl ester 、 phthalimidesulfenyl chloride 以 二氯甲烷 为溶剂， 反应 1.0h， 以42%的产率得到(2S,3S)-methyl 2-(tert-butoxycarbonylamino)-3-(1,3-dioxoisoindolin-2-ylthio)pent-4-enoate
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes

  摘要：

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.

  DOI：

  10.1021/jo2010878
• 作为产物：
  描述：

  (4R)-2,2-dimethyl-4-[(E)-3-trimethylsilanyl-propenyl]-oxazolidine-3-carboxylic acid tert-butyl ester 在 chromium(VI) oxide 、 碳酸氢钠 、 过碘酸 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R)-2-tert-butoxycarbonylamino-5-trimethylsilanyl-E-pent-3-enoic acid methyl ester
  参考文献：
  名称：

  New unsaturated amino acids containing an allylsilane moiety on the lateral chain

  摘要：

  New enantiomerically enriched polyfunctionalized allylsilanes have been obtained from the synthetic elaboration of naturally occurring serine. In particular, an oxazolidine bearing an allylsilane framework on the lateral chain proved to be a suitable precursor for the corresponding silylated vinyl glycine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.017

文献信息

• New unsaturated amino acids containing an allylsilane moiety on the lateral chain
  作者：Gianna Reginato、Alessandro Mordini、Patrick Meffre、Alice Tenti、Michela Valacchi、Kevin Cariou

  DOI：10.1016/j.tetasy.2006.02.017

  日期：2006.3

  New enantiomerically enriched polyfunctionalized allylsilanes have been obtained from the synthetic elaboration of naturally occurring serine. In particular, an oxazolidine bearing an allylsilane framework on the lateral chain proved to be a suitable precursor for the corresponding silylated vinyl glycine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes
  作者：Gianna Reginato、Bernardo Pezzati、Andrea Ienco、Gabriele Manca、Andrea Rossin、Alessandro Mordini

  DOI：10.1021/jo2010878

  日期：2011.9.16

  An efficient synthesis of various protected syn-beta-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral beta-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.