5-苯基硫代-2'-脱氧尿苷 | 100634-97-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-苯基硫代-2'-脱氧尿苷
• 英文名称: 5-phenylsulfanyl-2'-deoxyuridine
• 英文别名: 5-phenylthio-2'-deoxyuridine；5-(Phenylthio)-2'-deoxyuridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-phenylsulfanylpyrimidine-2,4-dione
• CAS: 100634-97-7
• 化学式: C₁₅H₁₆N₂O₅S
• 分子量: 336.368
• InChiKey: JAHLFAWFOKQUDC-DMDPSCGWSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-苯基硫代-2'-脱氧尿苷 在 吡啶 、 4-二甲氨基吡啶 、 TEA 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Facile Photocyclization Chemistry of 5-Phenylthio-2‘-deoxyuridine in Duplex DNA

  摘要：

  We report here the synthesis of 5-phenylthio-2 '-deoxyuridine (d(PhS)U), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d((PhS)UG) and d(PhS)U-bearing duplex ODNs with 254 nm light results in the facile formation of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the basis for the efficient preparation of a new class of duplex DNA with an extended pi system.

  DOI：

  10.1021/ol060659v
• 作为产物：
  描述：

  溴脲苷 、 苯硫酚 在 sodium 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以47.5%的产率得到5-苯基硫代-2'-脱氧尿苷
  参考文献：
  名称：

  Facile Photocyclization Chemistry of 5-Phenylthio-2‘-deoxyuridine in Duplex DNA

  摘要：

  We report here the synthesis of 5-phenylthio-2 '-deoxyuridine (d(PhS)U), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d((PhS)UG) and d(PhS)U-bearing duplex ODNs with 254 nm light results in the facile formation of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the basis for the efficient preparation of a new class of duplex DNA with an extended pi system.

  DOI：

  10.1021/ol060659v

文献信息

• Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides
  作者：Filip Botha、Michaela Slavíčková、Radek Pohl、Michal Hocek

  DOI：10.1039/c6ob01917j

  日期：——

  The syntheses of 5-arylsulfanyl- or 5-arylselanylpyrimidine and 7-arylsulfanyl- or 7-arylselanyl-7-deazapurine nucleosides and nucleotides were developed by the Cu-mediated sulfanylations or selanylations of the corresponding 5-iodopyrimidine or 7-iodo-7-deazapurine nucleosides or nucleotides with diaryldisulfides or -diselenides. The reactions were also applicable for direct modifications of 2′-deoxycytidine

  5-芳基硫烷基-或5-芳基硒基嘧啶和7-芳基硫烷基-或7-芳基硒基-7-脱氮嘌呤核苷和核苷酸的合成是通过相应的5-碘嘧啶或7-碘基-7-的铜介导的磺酰化或硒基化而开发的。脱氮嘌呤核苷或带有二芳基二硫化物或-二硒化物的核苷酸。该反应也可用于2'-脱氧胞苷三磷酸的直接修饰，并且所得的5-芳基硫烷基或5-芳基硒基-dCTP用作聚合酶合成底物的底物，所述DNA在主要凹槽中带有芳基硫烷基或芳基硒基。
• Palladium-mediated synthesis of C-5 pyrimidine nucleoside thioethers from disulfides and mercurinucleosides
  作者：Donald E. Bergstrom、Peter Beal、Jeffrey Jenson、Xiaoping Lin

  DOI：10.1021/jo00019a025

  日期：1991.9

  Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiodipropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5-[3-(methoxycarbonyl)-1-thiapropyl]-2'-deoxyuridine, and 5-[3-(trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine in yields ranging from 46 to 73%. Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10%). The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated.
• Hirota, Kosaku; Tomishi, Tetsuo; Maki, Yoshifumi, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 161 - 173
  作者：Hirota, Kosaku、Tomishi, Tetsuo、Maki, Yoshifumi、Sajiki, Hironao

  DOI：——

  日期：——
• Palladium-mediated coupling between organic disulfides and nucleic acid constituents
  作者：Don Bergstrom、Peter Beal、Adil Husain、Robert Lind、Jeffrey Jenson

  DOI：10.1021/ja00183a061

  日期：1989.1
• BERGSTROM, DON;BEAL, PETER;HUSAIN, ADIL;LIND, ROBERT;JENSON, JEFFREY, J. AMER. CHEM. SOC., 111,(1989) N, C. 374-375
  作者：BERGSTROM, DON、BEAL, PETER、HUSAIN, ADIL、LIND, ROBERT、JENSON, JEFFREY

  DOI：——

  日期：——