1-[(2R,3S,4S,5R)-3-Amino-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 1055042-33-5

• 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,4S,5R)-3-Amino-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3S,4S,5R)-3-amino-4-(2-hydroxyethylsulfonyl)-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1055042-33-5
• 化学式: C₃₀H₃₁N₃O₇S
• 分子量: 577.658
• InChiKey: XFHDSNMGWOHBFP-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,4S,5R)-3-Amino-4-(2-hydroxy-ethanesulfonyl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 1-((1R,3R,3aS,7aS)-7-Allyl-4,4-dioxo-3-trityloxymethyl-octahydro-2-oxa-4λ⁶-thia-7-aza-inden-1-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：

  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

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.