1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose | 149656-26-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose
• 英文别名: [(3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-phenylselanyloxolan-2-yl] acetate
• CAS: 149656-26-8
• 化学式: C₂₉H₃₄O₄SeSi
• 分子量: 553.632
• InChiKey: INYRCMCFNCZUJP-QFIHXRDCSA-N

物化性质

• 沸点：
  569.7±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose 在 ammonium sulfate 、 三乙基硼 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 4.75h， 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：

  (S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan 在 吡啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose
  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

• Synthesis and Biological Properties of the Four Optical Isomers of 5-<i>o</i>-Carboranyl-2′,3′-didehydro-2′,3′-dideoxyuridine
  作者：Jean-Christophe G. Graciet、Junxing Shi、Raymond F. Schinazi

  DOI：10.1080/07328319808004670

  日期：1998.4

  electron deficient 5-o-carboranyl moiety on uracil influenced the yield of the various isomers. In general, the compounds demonstrated weak anti-human immunodeficiency virus activity in primary human lymphocytes. No marked difference in the biological profile was noted for the various optical isomers, suggesting that the high lipophilicity of these nucleosides imparted by the carboranyl moiety overrides

  合成了5-o-碳烷基-2'，3'-二氢-2'，3'-二脱氧尿苷（d4CU）的四个异构体，并确定了它们在正常和癌细胞中的抗病毒活性和细胞毒性。在氧化消除和脱保护后，将所需的化合物甲硅烷基化的5-o-碳氧烷基尿嘧啶与受保护的D / L 2,3-二脱氧-2-苯基硒烯基核糖基乙酸酯偶联。尿嘧啶上电子缺陷的5-o-碳烷基部分的存在影响了各种异构体的产率。通常，这些化合物在原代人淋巴细胞中显示出弱的抗人免疫缺陷病毒活性。对于各种旋光异构体，没有观察到生物学特性的明显差异，
• Synthesis and Biological Evaluation of 2‘,3‘-Didehydro-2‘,3‘-dideoxy-5- fluorocytidine (D4FC) Analogues:  Discovery of Carbocyclic Nucleoside Triphosphates with Potent Inhibitory Activity against HIV-1 Reverse Transcriptase
  作者：Junxing Shi、J. Jeffrey McAtee、Susan Schlueter Wirtz、Phillip Tharnish、Amy Juodawlkis、Dennis C. Liotta、Raymond F. Schinazi

  DOI：10.1021/jm980510s

  日期：1999.3.1

  beta-D-D4FC was not active against HIV-1, even at 100 microM. The carbocyclic analogues (26a,b) of D4FC demonstrated weak activity against HIV-1 and no toxicity in various cells. The triphosphates (27a,b) of the carbocyclic nucleosides demonstrated potent inhibitory activity against recombinant HIV-1 reverse transcriptase at submicromolar concentrations. Of the compounds tested as potential anticancer

  发现了新型胞嘧啶核苷β-D-2'，3'-didehydro-2'，3'-二脱氧-5-氟胞苷（D-D4FC）作为有效的抗人免疫缺陷病毒（HIV）药物，这导致我们合成了一系列β-D-D4FC的类似物和衍生物，它们可能更具选择性，并且具有增强的糖苷键稳定性。评价合成的D-D4FC类似物在各种细胞中的抗HIV-1活性，抗癌活性和细胞毒性。生物学数据表明，β-D-D4FC被溴（6c）和碘（6d）5取代导致抗病毒活性丧失，并且D-D4FC的α-D异头物（7a）也没有活动。与母体化合物相比，D-D4FC的5-氟尿嘧啶类似物（6b和7b）效力更低，细胞毒性更高，而β-L-D4FU（11）则显示出强大的抗HIV-1活性和细胞毒性。β-D-D4FC的N4-和5'-O-酰基衍生物（17，15a-c）表现出与β-D-D4FC相当的抗病毒活性。相反，β-D-D4FC的N4-异丙基衍生物（20）即使在100 micr
• 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：——