1-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-lyxo-hexopyranosyl-2-ulose)thymine | 946496-64-6

• 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-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-lyxo-hexopyranosyl-2-ulose)thymine
• CAS: 946496-64-6
• 化学式: C₂₀H₃₂N₂O₇Si
• 分子量: 440.569
• InChiKey: CZWBMKXIPCYNAF-DUFGSWQCSA-N

反应信息

• 作为反应物：
  描述：

  1-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-lyxo-hexopyranosyl-2-ulose)thymine 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以79%的产率得到1-(β-D-lyxo-hexopyranosyl-2-ulose)thymine
  参考文献：
  名称：

  Exomethylene pyranonucleosides: Efficient synthesis and biological evaluation of 1-(2,3,4-trideoxy-2-methylene-β-d-glycero-hex-3-enopyranosyl)thymine

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.05.055
• 作为产物：
  描述：

  1-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-galactopyranosyl)thymine 在 重铬酸吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到1-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-β-D-lyxo-hexopyranosyl-2-ulose)thymine
  参考文献：
  名称：

  Exomethylene pyranonucleosides: Efficient synthesis and biological evaluation of 1-(2,3,4-trideoxy-2-methylene-β-d-glycero-hex-3-enopyranosyl)thymine

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.05.055