1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine | 128119-38-0

• 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: 1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine
• 英文别名: 5'-O(tert-butyldimethylsilyl)-3'-O-(1-imidazolylthiocarbonyl)thymidine；5'-TBDMS-3'-thiocarbonylimidazole-thymidine；O-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] imidazole-1-carbothioate
• CAS: 128119-38-0
• 化学式: C₂₀H₃₀N₄O₅SSi
• 分子量: 466.634
• InChiKey: OFFGVHNSASVVDV-ARFHVFGLSA-N

物化性质

• 熔点：
  105-108 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine 在 lanthanum(III) chloride 、 sodium periodate 、 四氧化锇 、 偶氮二异丁腈 、 氢氟酸 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成
  参考文献：
  名称：

  Polymerization on Solid Supports

  摘要：

  DOI：

  10.1002/1521-3773(20021202)41:23<4567::aid-anie4567>3.0.co;2-6
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(1-imidazolyl)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine
  参考文献：
  名称：

  AZT类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成

  摘要：

  描述了一种使用自由基化学方法将碳取代基引入3'-脱氧胸苷3'-位的有效方法。提出了该方法在AZT的两个紧密类似物3'-脱氧-3'-（2-丙炔基）胸苷和3'-氰甲基-3'-脱氧胸苷的合成中的应用。

  DOI：

  10.1016/s0040-4039(00)94577-5

文献信息

• Hexofuranosyl thymidines inserted into oligodeoxynucleotides via their two exocyclic hydroxy groups. Oligo synthesis and RNase H activity
  作者：Vyacheslav V. Filichev、Birte Vester、Erik B. Pedersen

  DOI：10.1016/j.bmc.2004.03.053

  日期：2004.6

  Hexofuranosyl nucleosides are considered as conformationally restricted acyclic nucleosides using a furanose ring to link the diol backbone to the nucleobase. The phosphoramidite of 1-(2,3-dideoxy-beta-D-erythro-hexofuranosyl)thymine was synthesized from thymidine with formation of a new stereocentre at C-5' and the nucleoside was used in oligodeoxynucleotide (ODN) synthesis. Binding of mixed sequence

  六呋喃糖基核苷被认为是使用呋喃糖环将二醇主链连接至核碱基的构象受限的无环核苷。从胸腺嘧啶合成1-（2,3-二脱氧-β-D-赤型-六呋喃糖基）胸腺嘧啶的亚磷酰胺，并在C-5'处形成新的立体中心，并将核苷用于寡脱氧核苷酸（ODN）的合成。与野生型寡核苷酸相比，混合序列ODN与互补DNA和RNA的结合显示出降低的亲和力。在poly alphaT序列的中间插入导致ODN / dA（14）双链体在低离子强度下稳定，但与d（alphaT）（14）/ dA（14）相比，在中等和高盐缓冲液中观察到了下降。β和呋喃呋喃糖基胸苷都可以被RNase H裂解3'的互补混合序列RNA
• 5′-<i>O</i>-TBDMS-3′-<i>O-</i>-(1<i>H</i>-Imidazole-1-Thiocarbonyl)thymidine: A Novel Intermediate for the Synthesis of 2,3′-Anhydrothymidine
  作者：Zaesung No、Shi Yong Ryu、Seong-Kie Kim、Jong Woong Ahn、Bok Ju Song、Keun Jae Kim

  DOI：10.1080/00032719808006488

  日期：1998.3.1

  Abstract Thermal or base-promoted conversion of 5′-O-TBDMS-3′-O-(1H-imidazole-1-thiocarbonyl)thymidine (1) afforded 5′-O-TBDMS-2,3′-anhydro-thymidine (2), a pivotal intermediate for the transformation of the 3′-hydroxy group of 2′-deoxyribonucleosides, in high yield.

  摘要 5'-O-TBDMS-3'-O-(1H-咪唑-1-硫代羰基)胸苷 (1) 的热或碱促进转化得到 5'-O-TBDMS-2,3'-脱水胸苷 ( 2)，高产率转化 2'-脱氧核糖核苷的 3'-羟基的关键中间体。
• DNA-Catalyzed Polymerization
  作者：Xiaoyu Li、Zheng-Yun J. Zhan、Rachel Knipe、David G. Lynn

  DOI：10.1021/ja017319j

  日期：2002.2.1

  Native DNA oligomers are shown to be stereoselective catalysts for the polymerization of 5'-amino-3'-acetaldehyde-modified thymidine/adenosine nucleosides through reductive amination. The reaction follows step-growth kinetics to read the encoded sequence and chain-length information in the antiparallel direction. Single mismatches in the template are selected against at a level of >100:1. A method is therefore established to translate biopolymer-encoded information stereoselectively into sequence- and chain-length specific synthetic polymers.
• Synthesis of 3′-C-substituted thymidine derivatives by free-radical techniques: scope and limitations
  作者：Derek Horton、Kuangmin Chen、Zaesung No、Howard C. Lee

  DOI：10.1016/j.carres.2006.11.015

  日期：2007.2

  The scope and limitations of radical-mediated 3'-C-substitution of pyrimidine nucleosides was evaluated with 5'-O-(tertbutyldimethylsilyl)thymidine or its tert-butyldiphenylsilyl analogue having thionoester or thionoamide groups at O-3', including (methylthio)thiocarbonyl, (phenoxy)thiocarbonyl, (pentafluorophenoxy)thiocarbonyl, and (1-imidazoiyl)thiocarbonyl. Their reaction with acrylonitrile, methyl acrylate, and allyltributyltin under radical-generating conditions affords corresponding 3'-C-alkylated products, together with the product of simple deoxygenation at C-3'. The conditions for optimizing the yield of 3'-C-substituted product are presented. (c) 2006 Elsevier Ltd. All rights reserved.
• FIANDOR, J.;HURYN, D. M.;SLUBOSKI, B.;TODARO, L. J.;TAM, S., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 1107-1108
  作者：FIANDOR, J.、HURYN, D. M.、SLUBOSKI, B.、TODARO, L. J.、TAM, S.

  DOI：——

  日期：——