(3R,5S)-N-tert-butoxycarbonyl-5-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-2-pyrrolidinone | 138871-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,5S)-N-tert-butoxycarbonyl-5-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-2-pyrrolidinone
• 英文别名: tert-butyl (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-2-oxopyrrolidine-1-carboxylate
• CAS: 138871-63-3
• 化学式: C₂₆H₃₅NO₅Si
• 分子量: 469.653
• InChiKey: FRUPQOFRBIEQSZ-SIKLNZKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 MoO5*pyridine*HMPA 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,5S)-N-tert-butoxycarbonyl-5-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-2-pyrrolidinone
  参考文献：
  名称：

  由α-氨基酸不对称合成；（S）-焦谷氨酸的一些反应

  摘要：

  给出了焦谷氨酸衍生物（10）在C-3，C-4和C-5处的反应。

  DOI：

  10.1016/0040-4039(91)80452-c

文献信息

• Synthesis of Pyrrolidinone PNA:  A Novel Conformationally Restricted PNA Analogue
  作者：Ask Püschl、Thomas Boesen、Guido Zuccarello、Otto Dahl、Stefan Pitsch、Peter E. Nielsen

  DOI：10.1021/jo001000k

  日期：2001.2.1

  To preorganize PNA for duplex formation, a new cyclic pyrrolidinone PNA analogue has been designed. In this analogue the aminoethylglycine backbone and the methylenecarbonyl linker are connected, introducing two chiral centers compared to PNA. The four stereoisomers of the adenine analogue were synthesized, and the hybridization properties of PNA decamers containing one analogue were measured against complementary DNA, RNA, and PNA strands. The (3S,5R) isomer was shown to have the highest affinity toward RNA, and to recognize RNA and PNA better than DNA. The (3S,5R) isomer was used to prepare a fully modified decamer which bound to rU(10) with only a small decrease in T-m(DeltaT(m)/mod = 1 degreesC) relative to aminoethylglycine PNA.
• Asymmetric synthesis from α-amino acids; some reactions of (S)-pyroglutamate
  作者：King-Chung Woo、Keith Jones

  DOI：10.1016/0040-4039(91)80452-c

  日期：1991.11

  Reactions at C-3, C-4, and C-5 of pyroglutamate derivative (10) are presented.

  给出了焦谷氨酸衍生物（10）在C-3，C-4和C-5处的反应。