1-(β-D-galactopyranosyl)thymine | 20183-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-galactopyranosyl)thymine
• 英文别名: 1-beta-d-Galactopyranosylthymine；5-methyl-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyrimidine-2,4-dione
• CAS: 20183-21-5
• 化学式: C₁₁H₁₆N₂O₇
• 分子量: 288.257
• InChiKey: RMXUFBPORJBBEZ-WASRKXDBSA-N

物化性质

• 密度：
  1.614±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(β-D-galactopyranosyl)thymine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 136.0h， 生成 1-<2-O-(4-methoxytrityl)-β-D-galactopyranosyl>thymine
  参考文献：
  名称：

  El-Kattan, Yahya; Gosselin, Gilles; Imbach, Jean-Louis, Journal of the Chemical Society. Perkin transactions I, 1994, # 10, p. 1289 - 1298

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到1-(β-D-galactopyranosyl)thymine
  参考文献：
  名称：

  环Sal法合成吡喃核苷-6'-三磷酸

  摘要：

  描述了使用 cycloSal 方法高产合成 pyranonucleoside-6'-triphosphates。通过应用我们为合成环Sal-（吡喃糖基-6）-磷酸酯而开发的合成路线，实现了活化的环Sal-吡喃核苷-6'-磷酸三酯的合成。该路线涉及区域选择性 6'-叔丁基二甲基甲硅烷基保护和甲硅烷基保护基团与芴基甲氧羰基 (Fmoc) 基团的交换。6'-Fmoc-保护的衍生物被选择性地转化为环Sal-三酯。然后通过与焦磷酸盐的“滴定样”反应，将它们非常有效地转化为三磷酸盐。首先通过离子交换进行简单纯化，然后进行反相 (RP) 柱层析，以非常好的收率得到三磷酸盐。

  DOI：

  10.1002/ejoc.201402047

文献信息

• Synthesis of 1-(β-D-Galactopyranosyl)Thymine-6′-<i>O</i>-Triphosphate – A Potential Probe to Generate Reactive Dialdehyde for DNA–Enzyme Cross-Linking
  作者：Anilkumar R. Kore、Bo Yang、Balasubramanian Srinivasan

  DOI：10.1080/15257770.2015.1037457

  日期：2015.9.2

  ne in 91% yield. Acetyl deprotection using methanolic ammonia afforded 1-(β-D-galactopyranosyl)thymine in 98% yield. The modified one-pot methodology was used to convert 1-(β-D-galactopyranosyl)thymine into 1-(β-D-galactopyranosyl)thymine-6′-O-triphosphate in 72% yield, which involves the formation of 1-(β-D-galactopyranosyl)thymine dichlorophosphoridate using POCl3 as the reagent at the monophosphorylation

  从O，O开始，描述了一种简明，简便而有效的合成1-（β-D-吡喃半乳糖基）胸腺嘧啶-6'- O-三磷酸酯的潜在探针，该探针可以生成用于DNA-酶交联应用的反应性二醛。-双（三甲基甲硅烷基）胸腺嘧啶。氯化锡促进1,2,3,4,6-五-O-乙酰基α-d吡喃半乳糖的糖基化与ö，Ö N'-双（三甲基硅烷基）胸腺嘧啶，从而产生1-形成（2,3， 4,6- O-四乙酰基-β-D-吡喃半乳糖基）胸腺嘧啶的产率为91％。用甲醇氨进行的乙酰基脱保护得到1-（β-D-吡喃半乳糖基）胸腺嘧啶，产率为98％。改进的一锅法用于将1-（β-D-吡喃半乳糖基）胸腺嘧啶转化为1-（β-D-吡喃半乳糖基）胸腺嘧啶-6'- O-三磷酸酯，产率为72％，涉及形成1-在单磷酸化步骤中使用POCl 3作为试剂的（β-D-吡喃半乳糖基）胸腺嘧啶二氯磷酸酯，然后与焦磷酸三丁铵反应并水解所得环状中间体。
• Stereospecific Vorbrueggen-like reactions of 1,2-anhydro sugars. An alternative route to the synthesis of nucleosides
  作者：Ken Chow、Samuel Danishefsky

  DOI：10.1021/jo00300a049

  日期：1990.6
• The Synthesis of Thymine Nucleosides^1,2
  作者：Donald W. Visser、Irving Goodman、Karl Dittmer

  DOI：10.1021/ja01185a082

  日期：1948.5
• Exomethylene pyranonucleosides: Efficient synthesis and biological evaluation of 1-(2,3,4-trideoxy-2-methylene-β-d-glycero-hex-3-enopyranosyl)thymine
  作者：George Agelis、Niki Tzioumaki、Tanja Botić、Avrelija Cencič、Dimitri Komiotis

  DOI：10.1016/j.bmc.2007.05.055

  日期：2007.8

  A new series of unsaturated pyranonucleosides with an exocyclic methylene group and thymine as heterocyclic base have been designed and synthesized. D-Galactose (1) was readily transformed in three steps into the corresponding 1-(beta-D-galactopyranosyl)thymine (2). Selective protection of the primary hydroxyl group of 2 with a t-butyldimethylsilyl (TBDMS) group, followed by specific acetalation, and oxidation gave 1-(6-O-t-butyldimethylsilyl-3,4-O-isopropylidene-beta-D-lyxo-hexopyranosyl-2-ulose)thymine (5). Wittig reaction of the ketonucleoside 5, deprotection and tritylation of the 6'-hydroxyl group gave 1-(2-deoxy-2-methylene-6-O-trityl-beta-D-lyxo-hexopyranosyl)thymine (9). Exomethylene pyranonucleoside 9 was converted to the olefinic derivative 10, which after detritylation afforded the title compound 1-(2,3,4-trideoxy-2-methylene-beta-D-glycero-hex-3-enopyranosyl)thymine (11). These novel synthesized compounds were evaluated for antiviral activity against rotaviral infection and cytotoxicity in colon cancer. As compared to AZT, compounds 1-(2-deoxy-2-methylene-beta-D-lyxo-hexopyranosyl)thymine (7) and 1-(beta-D-lyxo-hexopyranosyl-2-ulose)thymine (8) showed to be more efficient, in rotavirus infections and in treatment of colon cancer. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Pyranonucleoside-6′-triphosphates through the<i>cyclo</i>Sal-Method
  作者：Johanna Huchting、Chris Meier

  DOI：10.1002/ejoc.201402047

  日期：2014.6

  The high yielding synthesis of pyranonucleoside-6′-triphosphates by using the cycloSal-method is described. Synthesis of the activated cycloSal-pyranonucleoside-6′-phosphate triesters was achieved by applying a synthetic route that had been developed for the synthesis of cycloSal-(glycopyranosyl-6)-phosphates by us. The route involved regioselective 6′-tert-butyldimethylsilyl protection and exchange

  描述了使用 cycloSal 方法高产合成 pyranonucleoside-6'-triphosphates。通过应用我们为合成环Sal-（吡喃糖基-6）-磷酸酯而开发的合成路线，实现了活化的环Sal-吡喃核苷-6'-磷酸三酯的合成。该路线涉及区域选择性 6'-叔丁基二甲基甲硅烷基保护和甲硅烷基保护基团与芴基甲氧羰基 (Fmoc) 基团的交换。6'-Fmoc-保护的衍生物被选择性地转化为环Sal-三酯。然后通过与焦磷酸盐的“滴定样”反应，将它们非常有效地转化为三磷酸盐。首先通过离子交换进行简单纯化，然后进行反相 (RP) 柱层析，以非常好的收率得到三磷酸盐。