(2R,3R,3aR,5S,7R,7aR)-7-Acetoxy-2-(6-benzoylamino-purin-9-yl)-3-(2,2-dimethyl-propionyloxy)-hexahydro-furo[3,2-b]pyran-5-carboxylic acid isopropyl ester | 885623-56-3

• 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: (2R,3R,3aR,5S,7R,7aR)-7-Acetoxy-2-(6-benzoylamino-purin-9-yl)-3-(2,2-dimethyl-propionyloxy)-hexahydro-furo[3,2-b]pyran-5-carboxylic acid isopropyl ester
• CAS: 885623-56-3
• 化学式: C₃₀H₃₅N₅O₉
• 分子量: 609.636
• InChiKey: SXRMIVXIUQNFCD-QCIUGOESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aR,5S,7R,7aR)-7-Acetoxy-2-(6-benzoylamino-purin-9-yl)-3-(2,2-dimethyl-propionyloxy)-hexahydro-furo[3,2-b]pyran-5-carboxylic acid isopropyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (2R,3R,3aS,5S,7R,7aR)-2-(6-Benzoylamino-purin-9-yl)-3,7-dihydroxy-hexahydro-furo[3,2-b]pyran-5-carboxylic acid
  参考文献：
  名称：

  Short Synthesis of Octosyl Nucleosides

  摘要：

  Commercial 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose was converted to a protected bicyclic octosyl acid thioglycoside donor by a 10-step sequence that features an intramolecular ester enolate alkylation. Glycosylation of N-benzoyladenine and methyl uridne-5-carboxylate followed by deprotection gave the respective nucleosides "octosyl adenine" and octosyl acid A.

  DOI：

  10.1021/ol0600382
• 作为产物：
  描述：

  (3R,3aS,5S,7R,7aR)-7-Acetoxy-3-hydroxy-2-phenylsulfanyl-hexahydro-furo[3,2-b]pyran-5-carboxylic acid isopropyl ester 在 吡啶 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 23.5h， 生成 (2R,3R,3aR,5S,7R,7aR)-7-Acetoxy-2-(6-benzoylamino-purin-9-yl)-3-(2,2-dimethyl-propionyloxy)-hexahydro-furo[3,2-b]pyran-5-carboxylic acid isopropyl ester
  参考文献：
  名称：

  Short Synthesis of Octosyl Nucleosides

  摘要：

  Commercial 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose was converted to a protected bicyclic octosyl acid thioglycoside donor by a 10-step sequence that features an intramolecular ester enolate alkylation. Glycosylation of N-benzoyladenine and methyl uridne-5-carboxylate followed by deprotection gave the respective nucleosides "octosyl adenine" and octosyl acid A.

  DOI：

  10.1021/ol0600382