6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine | 141684-84-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine
• 英文别名: 6-chloro-9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl]-9H-purine；tert-butyl-[[(2S,5R)-5-(6-chloropurin-9-yl)oxolan-2-yl]methoxy]-diphenylsilane
• CAS: 141684-84-6
• 化学式: C₂₆H₂₉ClN₄O₂Si
• 分子量: 493.08
• InChiKey: COEWONYYYWAYID-SIKLNZKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(2S,5R)-5-(6-氯-9H-嘌呤-9-基)四氢-2-呋喃甲醇
  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：

  叔丁基二苯基氯硅烷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 ammonium sulfate 、 三乙基硼 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 二异丁基氢化铝 、 六甲基二硅氮烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 8.25h， 生成 6-chloro-9-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>-9H-purine
  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

文献信息

• CHU, CHUNG K.;BEACH, WARREN J. WARREN;BABU, J. RAMESH;JEONG, LAK SHIN;JEO+, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 423-426
  作者：CHU, CHUNG K.、BEACH, WARREN J. WARREN、BABU, J. RAMESH、JEONG, LAK SHIN、JEO+

  DOI：——

  日期：——