1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil | 6038-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil
• 英文别名: 1-(O³-methanesulfonyl-O⁵-trityl-β-D-threo-2-deoxy-pentofuranosyl)-1H-pyrimidine-2,4-dione；1-(5-O-Trityl-3-O-mesyl-β-D-2-deoxy-xylofuranosyl)uracil；1-(2-Desoxy-3'-O-mesyl-5'-O-trityl-β-D-lyxosyl)-uracil；[(2R,3R,5R)-5-(2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 6038-53-5
• 化学式: C₂₉H₂₈N₂O₇S
• 分子量: 548.617
• InChiKey: MYQXMTLALZTTFT-RGSZASNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 在 叠氮化锂 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 Navuridine
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside

  摘要：

  Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 microM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C X 100 value of 283.

  DOI：

  10.1021/jm00358a016
• 作为产物：
  描述：

  3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 28.0h， 生成 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside

  摘要：

  Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 microM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C X 100 value of 283.

  DOI：

  10.1021/jm00358a016

文献信息

• Process for the deoxygenation of nucleosides
  申请人：The University of Georgia Research Foundation, Inc.

  公开号：US05384396A1

  公开（公告）日：1995-01-24

  An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

  一种高效的去氧化核苷的过程，包括将羟基与3-卤代丙腈或2-硝基乙基卤代烷基和二硫化碳在碱性条件下反应，形成2'-或3'-(氰基乙硫或硝基乙硫)硫代羰基，然后通过还原消除并用氢取代。这种去氧化过程可用于需要消除2'-或3'-羟基的各种核苷合成，包括制备3'-取代-2',3'-二脱氧核苷，如3'-叠氮-3'-脱氧胸苷和3'-叠氮-2',3'-二脱氧尿苷。
• A facile method for deprotection of trityl ethers using column chromatography
  作者：Ashish K Pathak、Vibha Pathak、Lainne E Seitz、Kamal N Tiwari、Mohammad S Akhtar、Robert C Reynolds

  DOI：10.1016/s0040-4039(01)01645-8

  日期：2001.10

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Nucleosides. VI. The Introduction of Unsaturation into the Carbohydrate of a Pyrimidine Nucleoside <i>via</i> a 2,3′-Anhydro Bond
  作者：Jerome P. Horwitz、Jonathan. Chua、Irwin L. Klundt、Margaret A. DaRooge、Michael. Noel

  DOI：10.1021/ja01063a080

  日期：1964.5.5
• ——
  作者：LIN TAI-SHUN、 PRUSOFF W. H.

  DOI：——

  日期：——
• US5384396A
  申请人：——

  公开号：US5384396A

  公开（公告）日：1995-01-24