1-{(2R,3S,4R,5R)-3-Benzylamino-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethanesulfonyl]-5-trityloxymethyl-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione | 202260-03-5

• 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-{(2R,3S,4R,5R)-3-Benzylamino-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethanesulfonyl]-5-trityloxymethyl-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3S,4R,5R)-3-(benzylamino)-4-[2-[tert-butyl(dimethyl)silyl]oxyethylsulfonyl]-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 202260-03-5
• 化学式: C₄₃H₅₁N₃O₇SSi
• 分子量: 782.045
• InChiKey: RDIJRAWIIOGOHL-PLUOQXLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-{(2R,3S,4R,5R)-3-Benzylamino-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethanesulfonyl]-5-trityloxymethyl-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以90%的产率得到1-[(2R,3S,4R,5R)-3-Benzylamino-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Sugar-Modified Uridine Bisvinyl Sulfone:  Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization

  摘要：

  A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. The structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.

  DOI：

  10.1021/jo9705576
• 作为产物：
  描述：

  5’-O-三苯甲基尿苷-2’,3’-来苏-环氧化物 在 吡啶 、 咪唑 、 sodium hydroxide 、 magnesium monoperoxyphthalate hexahydrate 、 甲基磺酰氯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.5h， 生成 1-{(2R,3S,4R,5R)-3-Benzylamino-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethanesulfonyl]-5-trityloxymethyl-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Sugar-Modified Uridine Bisvinyl Sulfone:  Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization

  摘要：

  A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. The structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.

  DOI：

  10.1021/jo9705576

文献信息

• Sugar-Modified Uridine Bisvinyl Sulfone:  Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization
  作者：Sanjib Bera、Graham J. Langley、Tanmaya Pathak

  DOI：10.1021/jo9705576

  日期：1998.3.1

  A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. The structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.