1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine | 125440-15-5

• 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: 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine
• 英文别名: 1-[5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl]thymine；1-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylselanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 125440-15-5
• 化学式: C₃₂H₃₆N₂O₄SeSi
• 分子量: 619.694
• InChiKey: FFUNGIMABKVDLW-PDVBFRJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine 在 吡啶 、 四丁基氟化铵 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 司他夫定
  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：

  (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 在 吡啶 、 4-二甲氨基吡啶 、 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.33h， 生成 1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>thymine
  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

• Stereoselective Synthesis of 2‘,3‘-Dideoxynucleosides by Addition of Selenium Electrophiles to Glycals. A Formal Synthesis of D4T from 2-Deoxyribose
  作者：Yolanda Díaz、Anas El-Laghdach、M Isabel Matheu、Sergio Castillón

  DOI：10.1021/jo9616825

  日期：1997.3.1
• A highly stereoselective glycosylation of 2-(phenylselenenyl)-2,3-dideoxyribose derivative with thymine: synthesis of 3'-deoxy-2',3'-didehydrothymidine and 3'-deoxythymidine
  作者：Chung K. Chu、J. Ramesh Babu、J. Warren Beach、Soon K. Ahn、Haoqiang Huang、Lak S. Jeong、Sang J. Lee

  DOI：10.1021/jo00292a006

  日期：1990.3
• CHU, CHUNG K.;BABU, J. RAMESH;BEACH, J. WARREP;AHN, SOON K.;HUANG, HAOGIA+, J. ORG. CHEM., 55,(1990) N, C. 1418-1420
  作者：CHU, CHUNG K.、BABU, J. RAMESH、BEACH, J. WARREP、AHN, SOON K.、HUANG, HAOGIA+

  DOI：——

  日期：——
• 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：——
• A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides
  作者：J. Warren Beach、Hea O. Kim、Lak S. Jeong、Satyanarayana Nampalli、Qamrul Islam、Soon K. Ahn、J. Ramesh Babu、Chung K. Chu

  DOI：10.1021/jo00040a031

  日期：1992.7

  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.