3'-isothiocyanato-2',3'-dideoxythymidine | 130945-07-2

• 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: 3'-isothiocyanato-2',3'-dideoxythymidine
• 英文别名: 3'-deoxy-3'-isothiocyanatothymidine；Thymidine, 3'-deoxy-3'-isothiocyanato-；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isothiocyanatooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 130945-07-2
• 化学式: C₁₁H₁₃N₃O₄S
• 分子量: 283.308
• InChiKey: JFVVYUNTFDTCEH-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-isothiocyanato-2',3'-dideoxythymidine 在 氯化锑(V) 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5'-acetyl-2',3'-dideoxy-3'-(2,5-dihydro-5,5-dimethyl-[1,3,4]thiadiazolimino)thymidine
  参考文献：
  名称：

  3?-1,2,4-三唑并和 3?-1,3,4-噻二唑亚胺胸苷的合成

  摘要：

  通过自发重排，通过 5'-乙酰基-3'-脱氧-3'-异硫氰酸基胸苷 9 与 1-氮杂-2 的环加成反应制备了新的 5'-乙酰基-3'-1,3,4-噻二唑亚胺胸苷 11、14 -azoniaallene 六氯锑酸盐。类似地，3'-氰基类似物 19 与相同的枯草烯反应以提供 3'-1,2,4-三唑基-胸苷 22、24 和 26。解封酰化产物得到游离核苷。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:298–303, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10146

  DOI：

  10.1002/hc.10146
• 作为产物：
  描述：

  齐多夫定 以 1,4-二氧六环 为溶剂， 生成 3'-isothiocyanato-2',3'-dideoxythymidine
  参考文献：
  名称：

  Zehl, Andrea; Cech, Dieter, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S137 - S139

  摘要：

  DOI：

文献信息

• Synthesis of chemically reactive analogues of AZT and their biological evaluation against HIV
  作者：Stuart L. Schreiber、Norihiro Ikemoto

  DOI：10.1016/0040-4039(88)85124-4

  日期：1988.1

  Several 3'-deoxythymidine analogues were prepared and tested against HIV. The choice of analogues was based on their possible covalent binding to the enzyme reverse transcriptase.

  制备了几种3'-脱氧胸苷类似物，并针对HIV进行了测试。类似物的选择基于它们与酶逆转录酶的可能共价结合。
• Vandendriessche, Frank; Aerschot, Arthur Van; Voortmans, Martine, Journal of the Chemical Society. Perkin transactions I, 1993, # 14, p. 1567 - 1576
  作者：Vandendriessche, Frank、Aerschot, Arthur Van、Voortmans, Martine、Janssen, Gerard、Busson, Roger、et al.

  DOI：——

  日期：——
• Synthesis of 3′-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing
  作者：Karen Stolze、Ulrich Koert、Sven Klingel、Gregor Sagner、Regina Wartbichler、Joachim W. Engels

  DOI：10.1002/(sici)1522-2675(19990908)82:9<1311::aid-hlca1311>3.0.co;2-z

  日期：1999.9.8

  Two 3'-modified and three base-modified ddNTPs were synthesized and tested with several DNA polymerases for incorporation activity. Starting from 3'-azido-3'-deoxythymidine (AZT; 1), we were able to produce 3'-deoxy-3'-isocyanato-thymidine and 3'-deoxy-3'-isothiocyanatothymidine (3 and 4, resp,) in a rapid synthesis based on the solid-support approach (Scheme 1). These 3'-functionalities could be used to attach a spacer molecule via urea and thiourea groups, respectively. Since the thus-obtained tethered nucleotides 7 and 8 can be used to label with fluorescent dyes (cf. Scheme 5), they are convenient building blocks for practical applications in DNA sequencing. Furthermore, we synthesized, via 14 (Scheme 2), 17 (Scheme 3), and 19 (Scheme 4), the N-4-modified dideoxycytidine 5'-triphosphate dye derivatives 22, 23, and 24, respectively, with different lengths of linkers between the base residue and the dye (Scheme). Base-specific termination for the derivatives 22 and 23 was demonstrated (Fig. 2a and 2b).
• MATSUDA, AKIRA;SATOH, MUTSUMI;UEDA, TOHRU;MACHIDA, HARUHIKO;SASAKI, TAKUM+, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 587-597
  作者：MATSUDA, AKIRA、SATOH, MUTSUMI、UEDA, TOHRU、MACHIDA, HARUHIKO、SASAKI, TAKUM+

  DOI：——

  日期：——
• Zehl, Andrea; Cech, Dieter, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S137 - S139
  作者：Zehl, Andrea、Cech, Dieter

  DOI：——

  日期：——