1-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione | 202260-05-7

• 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-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(2R,3R,4S,5R)-4-[2-[tert-butyl(dimethyl)silyl]oxyethylsulfanyl]-3-hydroxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 202260-05-7
• 化学式: C₃₆H₄₄N₂O₆SSi
• 分子量: 660.907
• InChiKey: PARKSTKQXNJRKS-OMUYGTQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-dione 在 吡啶 、 四丁基氟化铵 、 magnesium monoperoxyphthalate hexahydrate 、 甲基磺酰氯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 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 咪唑 、 四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 生成 1-[3-S-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)-3-thio-5-O-(triphenylmethyl)-β-D-arabinofuranosyl]pyrimidine-2,4(1H,3H)-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

• Synthesis, Structure, and Conformation of 2′,3′-Fused Oxathiane and Thiomorpholine Uridines
  作者：Jingbo Sun、Jinchang Wu、Hua Yang

  DOI：10.1002/hlca.200790199

  日期：2007.10

  two 2′,3′-fused bicyclic nucleoside analogues, i.e., 1-[(4aR,5R,7R,7aS)-hexahydro-5-(hydroxymethyl)-4,4-dioxidofuro[3,4-b][1,4]oxathiin-7-yl]pyrimidine-2,4(1H,3H)-dione (1a) and 1-[(4aS,5R,7R,7aS)-hexahydro-7-(hydroxymethyl)-1,1-dioxido-2H-furo[3,4-b][1,4]thiazin-5-yl]pyrimidine- 2,4(1H,3H)-dione (1b), are described, the key step being an intramolecular hetero-Michael addition. Their structures and

  两个2'，3'稠合的双环核苷类似物，即1-[（（4a R，5 R，7 R，7a S）-六氢-5-（羟甲基）-4,4-dioxidofuro [3， 4- b ] [1,4]草苷-7-基]嘧啶-2,4（1 H，3 H）-二酮（1a）和1-[（4a S，5 R，7 R，7a S）-六氢-7-（羟甲基）-1,1-二氧化物-2 H-呋喃[3,4- b ] [1,4]噻嗪-5-基]嘧啶-2,4（1 H，3 H）-二酮（1b），其中关键步骤是分子内杂-迈克尔加成。使用1D和2D-NMR以及HR-MS分析，可以更详细地分析以前通过X射线晶体学解决的它们的结构和构象。