Diphenyl-phosphinic acid (2R,3S,5R)-5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethoxymethyl ester | 173034-02-1

• 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: Diphenyl-phosphinic acid (2R,3S,5R)-5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethoxymethyl ester
• 英文别名: 4-amino-1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-(diphenylphosphoryloxymethoxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
• CAS: 173034-02-1
• 化学式: C₃₉H₄₄N₃O₆PSi
• 分子量: 709.854
• InChiKey: WHPQVHZPNSMDOL-LIVOIKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-mercapto-5'-O-DMT-3'-deoxythymidine 、 Diphenyl-phosphinic acid (2R,3S,5R)-5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethoxymethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 formamide 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到1-[(2R,4S,5R)-4-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[tert-butyl(diphenyl)silyl]oxyoxolan-2-yl]methoxymethylsulfanyl]-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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：

  1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 1H-1,2,3-三氮唑 、 N-碘代丁二酰亚胺 、 氨 、 三乙胺 、 乙腈 、 三氯氧磷 、 过氧化苯甲酰 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 生成 Diphenyl-phosphinic acid (2R,3S,5R)-5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethoxymethyl 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 mild method for the syntheses of 3′-thioformacetal dinucleotides: The development of diphenylphosphinate as a glycosyl donor
  作者：Jiancun Zhang、Mark D. Matteucci

  DOI：10.1016/0040-4039(95)01809-v

  日期：1995.11

  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.