Benzoic acid 2-((2R,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ylsulfanyl)-ethyl ester | 202259-89-0

• 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,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ylsulfanyl)-ethyl ester
• 英文别名: 2-[[(2R,4R,5R,6R)-10-oxo-4-(trityloxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-5-yl]sulfanyl]ethyl benzoate
• CAS: 202259-89-0
• 化学式: C₃₇H₃₂N₂O₆S
• 分子量: 632.737
• InChiKey: KAOMSMWQDQAUEU-PKHTVCQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid 2-((2R,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ylsulfanyl)-ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 叠氮化锂 、 氢气 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~140.0 ℃ 、206.84 kPa 条件下， 反应 9.0h， 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 、 苯甲酰氯 、 2-巯基乙醇 生成 Benzoic acid 2-((2R,3R,3aR,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-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