N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>cytosine | 141684-80-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>cytosine
• 英文别名: N⁴-acetyl-1-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl]cytosine；N-[1-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylselanyloxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 141684-80-2
• 化学式: C₃₃H₃₇N₃O₄SeSi
• 分子量: 646.72
• InChiKey: JIFUTSVLENUAOJ-FPHQXIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>cytosine 在 三乙基硼 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 1.0h， 生成 2,3-二脱氧胞啶
  参考文献：
  名称：

  A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides

  摘要：

  A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

  DOI：

  10.1021/jo00040a031
• 作为产物：
  描述：

  (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.75h， 生成 N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>cytosine
  参考文献：
  名称：

  A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides

  摘要：

  A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.

  DOI：

  10.1021/jo00040a031