(1S,3S,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
• 英文别名: [(1S,3S,4S,7R)-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-7-phenylmethoxy-2-oxa-5-azabicyclo[2.2.1]heptan-1-yl]methyl methanesulfonate
• 化学式: C₁₉H₂₃N₃O₇S
• 分子量: 437.474
• InChiKey: SWVCRBGTWSNSFM-HIRMHNASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 、 sodium benzoate 在 15-冠醚-5 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 [(1S,3S,4S,7R)-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-7-phenylmethoxy-2-oxa-5-azabicyclo[2.2.1]heptan-1-yl]methyl benzoate
  参考文献：
  名称：

  Parallel RNA-strand recognition by 2′-amino-β-l-LNA

  摘要：

  A short synthetic route to the first beta-L-ribo configured locked nucleic acid (LNA), that is, 2'-amino-beta-L-LNA thymine phosphoramidite 6, has been developed from bicyclic nucleoside 1. Incorporation of 2'-amino-beta-L-LNA thymine monomers into alpha-DNA strands results in probes forming stable duplexes with complementary RNA in parallel orientation. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.079
• 作为产物：
  描述：

  4-(羟甲基)-1,2-O-异丙亚基-3-O-苄基-beta-L-苏式戊呋喃糖 在 吡啶 、 苯磺酰胺 、 sodium hydroxide 、 sodium azide 、 15-冠醚-5 、 硫酸 、 溶剂黄146 、 乙酰氯 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,3S,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane
  参考文献：
  名称：

  SYNTHESIS OF A 2′-AMINO-α-L-LNA-T PHOSPHORAMIDITE

  摘要：

  A convergent route to 2'-amino-alpha-L-LNA-T phosphoramidite building block 16 has been developed. Key steps include 1) introduction of a C2-azido group prior to nucleobase-coupling, 2) tandem Staudinger and intramolecular nucleophilic substitution reaction, and 3) separation of alpha-L- and beta-L-configured intermediates.

  DOI：

  10.1080/15257770500276866

文献信息

• Synthesis and Hybridization Studies of 2‘-Amino-α-L-LNA and Tetracyclic “Locked LNA”
  作者：T. Santhosh Kumar、Andreas S. Madsen、Jesper Wengel、Patrick J. Hrdlicka

  DOI：10.1021/jo060331f

  日期：2006.5.1

  render 2‘-amino-α-L-LNA a promising building block for nucleic acid based nanobiotechnology and therapeutics. A slight modification in strategy facilitated the synthesis of the corresponding phosphoramidite building blocks of Michael adducts, which due to their tetracyclic skeletons exhibit a conformationally restricted furanose ring and glycosidic torsion angle (anti-range). Incorporation of such

  已经开发了一种收敛到新型锁定核酸的途径，即2'-氨基-α-L-LNA。到相应的胸腺嘧啶亚磷酰胺结构单元的优化合成路线，从起始二醇开始，经过15个步骤，总收率为4％。关键合成步骤包括：（a）引入的C2-叠氮基的前核碱基偶联，（b）中的糖基化Vorbrüggen主要得到所需的α端基异构体，（C）α-分离升-核糖-和β-升-核糖-构型的双环核苷，和（d）选择合适的保护基以避免分子内迈克尔将C2'-氨基加成到C6-位上。将2'-氨基-α-L-LNA单体掺入寡脱氧核糖核苷酸中会导致互补DNA的热稳定性发生适度变化，而观察到RNA互补和出色的Watson-Crick判别可显着提高热稳定性。这些结果以及合成策略的灵活性允许在后期进行化学选择性N2'-功能化，使得2'-氨基-α-L-LNA成为基于核酸的纳米生物技术和治疗方法的有前途的构建基块。在策略上稍作修改，有助于合成迈克尔加合物的相应亚磷酰胺结构单元
• Parallel RNA-strand recognition by 2′-amino-β-l-LNA
  作者：T. Santhosh Kumar、Michael E. Østergaard、Pawan K. Sharma、Poul Nielsen、Jesper Wengel、Patrick J. Hrdlicka

  DOI：10.1016/j.bmcl.2009.03.079

  日期：2009.5

  A short synthetic route to the first beta-L-ribo configured locked nucleic acid (LNA), that is, 2'-amino-beta-L-LNA thymine phosphoramidite 6, has been developed from bicyclic nucleoside 1. Incorporation of 2'-amino-beta-L-LNA thymine monomers into alpha-DNA strands results in probes forming stable duplexes with complementary RNA in parallel orientation. (c) 2009 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF A 2′-AMINO-α-L-LNA-T PHOSPHORAMIDITE
  作者：Patrick J. Hrdlicka、T. Santhosh Kumar、Jesper Wengel

  DOI：10.1080/15257770500276866

  日期：2005.4.1

  A convergent route to 2'-amino-alpha-L-LNA-T phosphoramidite building block 16 has been developed. Key steps include 1) introduction of a C2-azido group prior to nucleobase-coupling, 2) tandem Staudinger and intramolecular nucleophilic substitution reaction, and 3) separation of alpha-L- and beta-L-configured intermediates.