Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-benzyloxy-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester | 189829-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-benzyloxy-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6R)-6-(2-acetamido-6-phenylmethoxypurin-9-yl)-3,4-diacetyloxy-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 189829-42-3
• 化学式: C₂₈H₂₉F₃N₆O₁₀
• 分子量: 666.568
• InChiKey: SRSZKGIGVIUIQT-PDRRETJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-benzyloxy-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 生成 N-[(2R,3R,4R,5S,6R)-2-(2-Amino-6-oxo-1,6-dihydro-purin-9-yl)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine)

  摘要：

  An unexpectedly low N-9/N-7 regioselectivity was obtained when Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine) was coupled with a D-glucosamine derivative under trimethylsilyl trifluoromethanesulfonate activation. An unprecedented solvent effect (toluene versus dichloroethane) on the N-9/N-7 ratio was also observed in the same study. The use of 2-N-acetyl-6-O-benzylguanine to successfully overcome the above regioselectivity problem is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00423-8
• 作为产物：
  描述：

  O-6-苄基鸟嘌呤 在 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(2-acetylamino-6-benzyloxy-purin-9-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine)

  摘要：

  An unexpectedly low N-9/N-7 regioselectivity was obtained when Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine) was coupled with a D-glucosamine derivative under trimethylsilyl trifluoromethanesulfonate activation. An unprecedented solvent effect (toluene versus dichloroethane) on the N-9/N-7 ratio was also observed in the same study. The use of 2-N-acetyl-6-O-benzylguanine to successfully overcome the above regioselectivity problem is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00423-8