1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil | 141192-09-8

• 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)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil
• 英文别名: 1-[5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl]uracil；1-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl]uracil；1-[(2R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 141192-09-8；141270-35-1
• 化学式: C₂₅H₃₀N₂O₄Si
• 分子量: 450.61
• InChiKey: LYSRPZPQFDYBJF-WMZHIEFXSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84.8%的产率得到2',3'-二脱氧尿苷
  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 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 6.33h， 生成 1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>uracil
  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

• Method for preparing 2'-3'-dideoxy-.beta.-nucleosides using
  申请人：Japan Tobacco, Incorporated

  公开号：US05416204A1

  公开（公告）日：1995-05-16

  2,3-Dideoxy-2,2-di(organothio)-B-D-pentofuranosyl-pyrimidines are disclosed as intermediates in the synthesis of 2', 3'-dideoxynucleosides and have the structure shown below. ##STR1## wherein R.sup.4 is a hydroxyl protecting group; X is oxygen or nitrogen, said nitrogen being bonded to a hydrogen atom, an alkyl or acyl group; Y is hydrogen, halogen, alkyl, haloalkyl or haloalkenyl; and R.sup.5 is alkyl, aralkyl, or aryl wherein aralkkyl or aryl is substituted with hydrogen, halogen, nitro or alkoxy. 2', 3'-Dideoxynucleosides, products of the above intermediates, are useful as antiviral agents.

  2,3-二去氧-2,2-二(有机硫)-B-D-戊呋喃核苷嘧啶是合成2',3'-二去氧核苷的中间体，具有以下结构。其中R^4是羟基保护基；X是氧或氮，所述氮与氢原子、烷基或酰基结合；Y是氢、卤素、烷基、卤代烷基或卤代烯基；R^5是烷基、芳基烷基或芳基，其中芳基烷基或芳基被氢、卤素、硝基或烷氧基取代。上述中间体的产物2',3'-二去氧核苷可用作抗病毒剂。
• 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.