α-(5'-O-tert-Butyldimethylsilyl)thymidine | 164070-17-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: α-(5'-O-tert-Butyldimethylsilyl)thymidine
• 英文别名: 1-((2S,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione；TBDMS(-5)2-deoxy-D-eryPenf(a)-thymin-1-yl；1-[(2S,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 164070-17-1
• 化学式: C₁₆H₂₈N₂O₅Si
• 分子量: 356.494
• InChiKey: IJWIJLIIOKZJMS-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-(5'-O-tert-Butyldimethylsilyl)thymidine 在 吡啶 、 四丁基氟化铵 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 3'-O-(4,4'-dimethoxytrityl)-α-thymidine
  参考文献：
  名称：

  5'-END DERIVATIVES

  摘要：

  本发明提供了式（1）的化合物。发明的另一个方面涉及抑制细胞中基因表达的方法，该方法包括（a）将本发明的寡核苷酸与细胞接触；以及（b）维持从步骤（a）中的细胞足够时间以获得目标基因mRNA的降解。

  公开号：

  US20130323836A1
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 Alpha-胸苷 在 吡啶 作用下， 生成 α-(5'-O-tert-Butyldimethylsilyl)thymidine
  参考文献：
  名称：

  5'-END DERIVATIVES

  摘要：

  本发明提供了式（1）的化合物。发明的另一个方面涉及抑制细胞中基因表达的方法，该方法包括（a）将本发明的寡核苷酸与细胞接触；以及（b）维持从步骤（a）中的细胞足够时间以获得目标基因mRNA的降解。

  公开号：

  US20130323836A1

文献信息

• [EN] NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS<br/>[FR] NOUVEAUX RÉACTIFS À BASE DE PHOSPHORE (V), LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LA FABRICATION DE COMPOSÉS ORGANOPHOSHOREUX (V) STÉRÉODÉFINIS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019200273A1

  公开（公告）日：2019-10-17

  The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.

  本发明涉及新型磷（V）（P(V)）试剂，其制备方法以及利用这种新型试剂制备有机磷（V）化合物的方法。
• Synthesis and Physicochemical Properties of Alternating .alpha.,.beta.-Oligodeoxyribonucleotides with Alternating (3'.fwdarw.3')- and (5'.fwdarw.5')-Internucleotidic Phosphodiester Linkages
  作者：Masakazu Koga、Andrzej Wilk、Michael F. Moore、Carlo L. Scremin、Liang Zhou、Serge L. Beaucage

  DOI：10.1021/jo00111a009

  日期：1995.3

  A simple and straightforward synthesis of alpha-2'-deoxycytidine and alpha-2'-deoxyadenosine derivatives 6a,b has been achieved from commercial N-4-benzoyl-beta-2'-deoxycytidine and N-6-benzoyl-beta-2'-deoxyadenosine, respectively. Properly protected alpha-2'-deoxyribonucleosides 8a-d were converted to the corresponding 5'-phosphoramidite derivatives 9a-d. These and commercial beta-2'-deoxyribonucleoside 3'-phosphoramidites were readily incorporated into alternating alpha,beta-oligodeoxyribonucleotides with alternating (3'-->3')- and (5'-->5')-internucleotidic phosphodiester linkages by standard solid-phase synthesis methods. The alpha,beta-oligodeoxyribonucleotide 12 (Scheme 3) was considerably more resistant to hydrolysis catalyzed by snake venom phosphodiesterase, calf spleen phosphodiesterase, and S1 nuclease than the parent unmodified oligonucleotide 17 (Table 2). Thermal stability of the complex composed of 12 and complementary unmodified beta-oligomer 18 was comparable to that measured for the hybrid composed of the beta-oligodeoxyribonucleoside phosphorothioate 20 and 18 but less than that of the native DNA duplex 17:18 (Table 3). The differences in thermal stability (Delta T-m) and free energy of dissociation (Delta Delta G(37)degrees) observed between the duplex 12:18 and the singly mismatched complex 12:19 (9 degrees C and -2.5 kcal/mol, respectively) (Tables 3 and 4) suggest that the sequence specificity;of 12 toward a complementary unmodified beta-DNA oligomer is comparable to that of 17. In addition, the CD spectrum of 12:18 at 22 degrees C resembles more closely that of the natural DNA duplex 17:18 than that of the alpha,beta-DNA duplex 12:13 (Figure 3). These findings indicate that the duplex 12:18 exhibits, at least to some extent, a B-type helicity. The alpha,beta-oligodeoxyribonucleotide 12 formed also a complex with the complementary beta-oligoribonucleotide 23 but with much reduced affinity (T-m = 35 degrees C) than that measured with the complementary DNA sequence 18 (T-m = 54 degrees C). CD spectroscopy indicated that the complex 12:23 adopted a conformation similar to that observed for duplex 17:23 at 22 degrees C. Unlike the DNA-RNA heteroduplex 17:23, the complex 12:23 was not a substrate for E. coli RNase H.