Benzoic acid 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylsulfanyl]-ethyl ester | 202260-06-8

• 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: Benzoic acid 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylsulfanyl]-ethyl ester
• 英文别名: 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl]sulfanylethyl benzoate
• CAS: 202260-06-8
• 化学式: C₃₇H₃₃N₅O₆S
• 分子量: 675.765
• InChiKey: UNCSLNRNUBGQJC-DWNQJFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Benzoic acid 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylsulfanyl]-ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 6.0h， 生成 1-[(2R,3S,4S,5R)-3-Amino-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 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 Benzoic acid 2-[(2R,3S,4S,5R)-4-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-ylsulfanyl]-ethyl ester
  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.