3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-fluoro-α-D-glucopyranosyl)-N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-(p-methoxybenzyl)adenosine | 1093280-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-fluoro-α-D-glucopyranosyl)-N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-(p-methoxybenzyl)adenosine
• 英文别名: [(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-[(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-3-yl]oxy-5-fluorooxan-2-yl]methyl acetate
• CAS: 1093280-56-8
• 化学式: C₅₃H₅₈FN₅O₁₃Si
• 分子量: 1020.15
• InChiKey: ZABQBIGKGONSDD-WCNRAGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  73
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  207
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-fluoro-α-D-glucopyranosyl)-N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-(p-methoxybenzyl)adenosine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以70%的产率得到3'-O-(2''-deoxy-2''-fluoro-α-D-glucopyranosyl)-5'-O-(tert-butyldiphenylsilyl)-2'-O-(p-methoxybenzyl)adenosine
  参考文献：
  名称：

  Towards the preparation of 2″-deoxy-2″-fluoro-adenophostin A. Study of the glycosylation reaction

  摘要：

  The synthesis of 2 ''-deoxy-2 ''-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2 ''-deoxy-2 ''-fluoroglycoside with excellent alpha-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.014
• 作为产物：
  描述：

  N-[9-[(2R,3R,4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-3-[(4-methoxyphenyl)methoxy]oxolan-2-yl]purin-6-yl]benzamide 、 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 以58%的产率得到3'-O-(3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-fluoro-α-D-glucopyranosyl)-N⁶-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2'-O-(p-methoxybenzyl)adenosine
  参考文献：
  名称：

  Towards the preparation of 2″-deoxy-2″-fluoro-adenophostin A. Study of the glycosylation reaction

  摘要：

  The synthesis of 2 ''-deoxy-2 ''-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2 ''-deoxy-2 ''-fluoroglycoside with excellent alpha-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.014