tert-butyl (3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-3-(phenylmethoxymethoxy)pyrrolidine-1-carboxylate | 329005-66-5

• 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: tert-butyl (3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-3-(phenylmethoxymethoxy)pyrrolidine-1-carboxylate
• CAS: 329005-66-5
• 化学式: C₃₄H₄₃NO₆Si
• 分子量: 589.804
• InChiKey: UZJTWBSHMOHWTR-OFSOJUDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-3-(phenylmethoxymethoxy)pyrrolidine-1-carboxylate 在 10percent Pd/C 、 10percent Pd(OH)2/C sodium azide 、 氢气 、 sodium hydride 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 16.88h， 生成 Benzoic acid (3R,5R)-5-(tert-butoxycarbonylamino-methyl)-1-methoxycarbonylmethyl-2-oxo-pyrrolidin-3-yl ester
  参考文献：
  名称：

  Synthesis of Pyrrolidinone PNA:  A Novel Conformationally Restricted PNA Analogue

  摘要：

  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.

  DOI：

  10.1021/jo001000k
• 作为产物：
  描述：

  苄基氯甲基醚 、 (5R)-N-tert-butoxycarbonyl-5-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-2-pyrrolidinone 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到tert-butyl (3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-3-(phenylmethoxymethoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Pyrrolidinone PNA:  A Novel Conformationally Restricted PNA Analogue

  摘要：

  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.

  DOI：

  10.1021/jo001000k

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.