1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine | 119794-55-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
• 英文别名: 5'-O-(tert-butyldimethylsilyl)-5-methyl-2',3'-didehydro-2',3'-dideoxyuridine；1-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 119794-55-7
• 化学式: C₁₆H₂₆N₂O₄Si
• 分子量: 338.479
• InChiKey: ACPBTLJVFDSART-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到司他夫定
  参考文献：
  名称：

  合成 2',3'-双脱氧核苷和 2',3'-Didehydro-2',3'-双脱氧核苷衍生物的可持续方案

  摘要：

  将核糖核苷转化为 2',3'-二脱氧核苷和 2',3'-二脱氢-2',3'-二脱氧核苷衍生物的改进方案，包括抗 HIV 药物司他夫定 (d4T)、扎西他滨 (ddC) 和去羟肌苷 (ddI) 成立。该过程涉及使用环保和低成本的试剂对黄原酸盐进行自由基脱氧。溴乙烷或 3-溴丙腈是制备核糖核苷 2',3'-双黄原酸酯的首选烷化剂。在随后的自由基脱氧反应中，三（三甲基甲硅烷基）硅烷和 1,1'-偶氮二（环己烷甲腈）分别被用来代替有害的 Bu 3 SnH 和 AIBN。此外，在 5'- O的脱保护步骤中，TBAF 取代了樟脑磺酸。-甲硅烷基醚基团和一种酶（腺苷脱氨酶）用于将 2',3'-二脱氧腺苷转化为 2',3'-二脱氧肌苷 (ddI)，产率很高。

  DOI：

  10.3390/molecules27133993
• 作为产物：
  描述：

  1-(3-iodo-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of (3′R)-3′-deoxy-3′-C-nitromethylthymidine

  摘要：

  DOI：

  10.1016/0008-6215(95)00003-c

文献信息

• Stereoselective Preparation of 1-[5-<i>O</i>-(<i>tert</i>-Butyldimethylsilyl)-2,3-dideoxy-3-iodo-β-<scp>D</scp>-<i>threo</i>-pentofuranosyl]thymine from Thymidine: An Efficient Entry to 3′,4′-Unsaturated Nucleoside
  作者：Yutaka Kubota、Kohji Nakamura、Kazuhiro Haraguchi、Hiromichi Tanaka

  DOI：10.1080/00397910903161751

  日期：2010.5.19

  The title compound (13) has been synthesized from 5′-O-TBS-thymidine (8) through a highly stereoselective iodination of the 3′-hydroxyl group utilizing I2/PPh3/imidazole. This method provides an efficient entry to the 3′,4′-unsaturated derivative (7).

  标题化合物 (13) 是由 5'-O-TBS-胸苷 (8) 通过使用 I2/PPh3/咪唑对 3'-羟基进行高度立体选择性碘化而合成的。该方法提供了对 3',4'-不饱和衍生物 (7) 的有效入口。
• General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides
  作者：C. K. Chu、V. S. Bhadti、B. Doboszewski、Z. P. Gu、Y. Kosugi、K. C. Pullaiah、P. Van Roey

  DOI：10.1021/jo00270a036

  日期：1989.4
• NEW 3′-DEOXYTHYMIDINES BEARING A NUCLEOPHILIC 3′-SUBSTITUENT
  作者：Anatoly M. Belostotskii、Helen Keren-Yeshuah、Jael Lexner、Alfred Hassner

  DOI：10.1081/ncn-100001439

  日期：2001.2.26

  New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3'-thio- and 3'- as well as 5'-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for-3'-alpha -alkylthiothymidines.
• Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Hideaki Maeda、Yoshiharu Itoh、Shigeru Saito、Tadashi Miyasaka

  DOI：10.1021/jo00018a038

  日期：1991.8

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.
• CHU, C. K.;BHADTI, V. S.;DOBOSZEWSKI, B.;GU, Z. P.;KOSUGI, Y.;PULLAIAH, K+, J. ORG. CHEM., 54,(1989) N, C. 2217-2225
  作者：CHU, C. K.、BHADTI, V. S.、DOBOSZEWSKI, B.、GU, Z. P.、KOSUGI, Y.、PULLAIAH, K+

  DOI：——

  日期：——