1-(3'-azido-2',3',5'-trideoxy-β-D-allofuranosyl)thymine | 130481-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3'-azido-2',3',5'-trideoxy-β-D-allofuranosyl)thymine
• 英文别名: 1-(3'-Azido-2',3',5'-trideoxy-beta-D-allofuranosyl)thymine；1-[(2R,4S,5R)-4-azido-5-(2-hydroxyethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 130481-61-7
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: ZUYSJOBAOKXRAG-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3'-azido-2',3',5'-trideoxy-β-D-allofuranosyl)thymine 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以57.7%的产率得到2-((2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)acetic acid
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 吡啶 、 甲醇 、 sodium azide 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 9-硼双环[3.3.1]壬烷 、 三苯基膦 、 三氟乙酸 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 环己烯 为溶剂， 反应 70.33h， 生成 1-(3'-azido-2',3',5'-trideoxy-β-D-allofuranosyl)thymine
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042

文献信息

• Side-chain derivatives of biologically active nucleosides. Part 1. Side-chain analogs of 3'-azido-3'-deoxythymidine (AZT)
  作者：Johann Hiebl、Erich Zbiral、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00094a014

  日期：1992.8

  beta-L-talofuranose 13. Coupling of these sugar derivatives with thymine gave the beta-nucleoside derivatives 18A-E. Treatment of compounds 18A-E with DBU produced the corresponding 2,3'-anhydro nucleosides 19A-E with a free 2'-OH group. After deoxygenation of 2'-O-[[(4-methylphenyl)oxy]thiocarbonyl] compounds 20A-E with tributyltin hydride the 2,3'-anhydro bridge of the 2'-deoxynucleosides 21A-E was opened

  从3-O-甲磺酰基-1,2-O-异亚丙基-α-D-氟呋喃糖（9）开始，将必要的碳水化合物1,2-二-O-乙酰基-6-O-苯甲酰基-5-脱氧的异头混合物-3-O-甲酰基-D-呋喃糖酶++ + 17A alpha / beta，1,2-二-O-乙酰基-5,6-二-O-苯甲酰基-3-O-甲酰基-D-呋喃糖酶17B alpha / beta，合成了1,2-二-O-乙酰基-5,6-二-O-苯甲酰基-3-O-甲磺酰基-L-呋喃呋喃糖酶17C alpha / beta。从6-脱氧获得1,2-二-O-乙酰基-5-O-苯甲酰基-6-脱氧-3-O-甲磺酰基-D-呋喃糖酶++ + 17D alpha / beta和相应的L-全呋喃糖酶17E alpha / beta -3,5-二-O-苯甲酰基-1,2-O-异亚丙基-α-D-呋喃糖（12）和相应的β-L-talofuranose13。将这些糖衍生物与胸腺嘧啶偶联
• 1- ( 3′- azido-2′, 3′, 5′ - trideoxy- [β - d .Allofuranosyl) thymine a side-chain homologue of 3′- azido - 3′- deoxythymidine
  作者：Johann Hiebl、Erich Zbiral

  DOI：10.1016/s0040-4039(00)94484-8

  日期：1990.1
• Synthesis of 3′-azido-5′-homothymidine analogs
  作者：Claudie Gautier、Rolande Leroy、Claude Monneret、Pierre Roger

  DOI：10.1016/s0040-4039(00)92706-0

  日期：1991.7

  1-(3'-azido-2',3',5'-trideoxy-beta-D-allofuranosyl) thymine 13, and 1-(3'-azido-3',5'-dideoxy-beta-D-(glucofuranosyl) thymine 20 and its 2'-O-methyl ether 22 were synthesized starting from 1,2-O-isopropylidene-alpha-D-glucopyranose and from 1,2-O-isopropylidene-alpha-D-allofuranose, respectively.
• HIEBL, JOHANN;ZBIRAL, ERICH, TETRAHEDRON LETT., 31,(1990) N8, C. 4007-4010
  作者：HIEBL, JOHANN、ZBIRAL, ERICH

  DOI：——

  日期：——
• HIEBL, JOHANN;ZBIRAL, ERICH;BALZARINI, JAN;DE, CLERCQ ERIC, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 521-522
  作者：HIEBL, JOHANN、ZBIRAL, ERICH、BALZARINI, JAN、DE, CLERCQ ERIC

  DOI：——

  日期：——