5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine | 139212-95-6

• 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: 5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine
• 英文别名: Mes(-3)[TBDPS(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methanesulfonate
• CAS: 139212-95-6
• 化学式: C₂₇H₃₄N₂O₇SSi
• 分子量: 558.728
• InChiKey: NJBKLJWUYJSKNF-RBZQAINGSA-N

物化性质

• 熔点：
  76 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine 在 4-二甲氨基吡啶 、 sodium hydroxide 、 二乙胺基三氟化硫 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 3’-脱氧-3-氟胸苷
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′‐Dideoxynucleosides

  摘要：

  A series of 5-(trifluoroethoxymethyl)-2',3'-dideoxyuridines and 5-[bis(trifluorroethoxy)-methyl]-2', 3'-dideoxyuri dines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]- derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.

  DOI：

  10.1081/ncn-120027814
• 作为产物：
  描述：

  methyl-5-O-tert-butyldiphenylsilyl-2-deoxy-ribo-furanoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 6.0h， 生成 5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine
  参考文献：
  名称：

  2'，3'-didehydro-2'，3'-dideoxynucleosides的新合成。

  摘要：

  3'-碘核苷4和3'-O-甲基磺酰基胸苷9是通过将甲硅烷基化的尿嘧啶2与5-O-叔丁基二苯甲硅烷基-2,3-二脱氧-3-碘-D-苏-戊呋喃糖苷缩合而合成的（3）和甲基5-O-叔丁基二苯基甲硅烷基-2-脱氧-3-甲基磺酰基-D-季戊基呋喃呋喃糖苷（8）。在用甲醇钠处理的消除反应中，核苷4和9产生了相应的2'，3'-二氢-2'，3'-二脱氧核苷5。化合物5b对HIV-1没有抗病毒活性。

  DOI：

  10.3891/acta.chem.scand.45-1060

文献信息

• New Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides.
  作者：Ahmed E. S. Abdel-Megied、Poul Hansen、Erik B. Pedersen、Carsten M. Nielsen、Hugh Brian Dunford、Nils Åge Frøystein、George W. Francis、Britt Karlsson

  DOI：10.3891/acta.chem.scand.45-1060

  日期：——

  The 3'-iodonucleoside 4 and the 3'-O-methylsulfonylthymidine 9 have been synthesized by condensation of silylated uracils 2 with methyl 5-O-tert-butyldiphensilyl-2,3-dideoxy-3-iodo-D-threo-pentofuran oside (3) and methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-methylsulfonyl-D-erythro- pentofuranoside (8), respectively. The nucleoside 4 and 9 produced the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides

  3'-碘核苷4和3'-O-甲基磺酰基胸苷9是通过将甲硅烷基化的尿嘧啶2与5-O-叔丁基二苯甲硅烷基-2,3-二脱氧-3-碘-D-苏-戊呋喃糖苷缩合而合成的（3）和甲基5-O-叔丁基二苯基甲硅烷基-2-脱氧-3-甲基磺酰基-D-季戊基呋喃呋喃糖苷（8）。在用甲醇钠处理的消除反应中，核苷4和9产生了相应的2'，3'-二氢-2'，3'-二脱氧核苷5。化合物5b对HIV-1没有抗病毒活性。
• Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′‐Dideoxynucleosides
  作者：Piyush Kumar、Kazue Ohkura、Jan Balzarini、Erik De Clercq、Koh‐ichi Seki、Leonard I. Wiebe

  DOI：10.1081/ncn-120027814

  日期：2004.1.1

  A series of 5-(trifluoroethoxymethyl)-2',3'-dideoxyuridines and 5-[bis(trifluorroethoxy)-methyl]-2', 3'-dideoxyuri dines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]- derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.