Benzoic acid (2R,3S,5R)-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-methylsulfanylmethoxymethyl-tetrahydro-furan-3-yl ester | 173033-98-2

• 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: Benzoic acid (2R,3S,5R)-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-methylsulfanylmethoxymethyl-tetrahydro-furan-3-yl ester
• CAS: 173033-98-2
• 化学式: C₂₃H₂₇N₅O₆S
• 分子量: 501.563
• InChiKey: HZCFCDFKSXFMMB-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  137.43
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,5R)-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-methylsulfanylmethoxymethyl-tetrahydro-furan-3-yl ester 在 N-碘代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 formamide 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A mild method for the syntheses of 3′-thioformacetal dinucleotides: The development of diphenylphosphinate as a glycosyl donor

  摘要：

  A mild and efficient procedure for the syntheses of 3'-thioformacetal dinucleotides is presented. The glycosylation synthon agent, diphenylphosphinate formacetal was developed as the intermediate for the coupling reaction under mild basic conditions. This method is compatible with purine deoxyribosides, unprotected amino groups and acid labile functionalities.

  DOI：

  10.1016/0040-4039(95)01809-v
• 作为产物：
  描述：

  二甲基硫 、 3'-O-苯甲酰基-2'-脱氧-N-异丁酰基鸟苷 在 过氧化苯甲酰 作用下， 以75%的产率得到Benzoic acid (2R,3S,5R)-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-methylsulfanylmethoxymethyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A mild method for the syntheses of 3′-thioformacetal dinucleotides: The development of diphenylphosphinate as a glycosyl donor

  摘要：

  A mild and efficient procedure for the syntheses of 3'-thioformacetal dinucleotides is presented. The glycosylation synthon agent, diphenylphosphinate formacetal was developed as the intermediate for the coupling reaction under mild basic conditions. This method is compatible with purine deoxyribosides, unprotected amino groups and acid labile functionalities.

  DOI：

  10.1016/0040-4039(95)01809-v

文献信息

• A practical stereoselective synthesis of (2S, 4S)-4-tert-butoxycarbonylamino-2-methylpyrrolidine
  作者：Qun Li、Daniel T.W. Chu、Kathleen Raye、Akiyo Claiborne、Louis Seif、Bryan Macri、Jacob J. Plattner

  DOI：10.1016/0040-4039(95)01813-w

  日期：1995.11

  Two practical syntheses of (2S, 4S)-4-tert-butoxycarbonylamino-2-methylpyrrolidine, an important intermediate for quinolone antibacterial agents, have been developed through the combination of diastereo and enantioselective reactions starting from ethyl crotonate and L-alanine, respectively.