(2R,3R)-3-benzoyloxy-3-cyano-2-dimethoxymethyltetrahydrofuran | 287183-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-benzoyloxy-3-cyano-2-dimethoxymethyltetrahydrofuran
• 英文别名: [(2R,3R)-3-cyano-2-(dimethoxymethyl)oxolan-3-yl] benzoate
• CAS: 287183-62-4
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: ICOPZYYZGVKHBS-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-benzoyloxy-3-cyano-2-dimethoxymethyltetrahydrofuran 在 盐酸 、 羟胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 生成 5-phenyl-3-(2'-hydroxymethyl-4',5'-dihydrofuran-3'-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 5-substituted-3-[(2′ S ,3′ S )-3′-hydroxy-2′-hydroxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazoles and their epimers

  摘要：

  5-Phenyl-3-[(2' R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10a and its epimer 11a, 5-methyl-3-[(2' R,3' S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyanohydrin benzoates 8a, 9a and cyanohydrin acetates 8b, 9b, respectively, by treatment with hydroxylamine in methanol via intramolecular transacylation and subsequent cyclization of the corresponding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a, 13a, 12b and 13b, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00095-1
• 作为产物：
  描述：

  2-(S)-dimethoxymethyl-3-keto-tetrahydrofuran 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R)-3-benzoyloxy-3-cyano-2-dimethoxymethyltetrahydrofuran
  参考文献：
  名称：

  Synthesis of 5-substituted-3-[(2′ S ,3′ S )-3′-hydroxy-2′-hydroxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazoles and their epimers

  摘要：

  5-Phenyl-3-[(2' R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10a and its epimer 11a, 5-methyl-3-[(2' R,3' S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyanohydrin benzoates 8a, 9a and cyanohydrin acetates 8b, 9b, respectively, by treatment with hydroxylamine in methanol via intramolecular transacylation and subsequent cyclization of the corresponding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a, 13a, 12b and 13b, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00095-1

文献信息

• Synthesis of 5-substituted-3-[(2′ S ,3′ S )-3′-hydroxy-2′-hydroxymethyltetrahydrofuran-3′-yl]-1,2,4-oxadiazoles and their epimers
  作者：W.D Wu、L.T Ma、L.H Zhang、Y Lu、F Guo、Q.T Zheng

  DOI：10.1016/s0957-4166(00)00095-1

  日期：2000.4

  5-Phenyl-3-[(2' R,3'S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10a and its epimer 11a, 5-methyl-3-[(2' R,3' S)-3'-hydroxy-2'-dimethoxymethyltetrahydrofuran-3'-yl]-1,2,4-oxadiazole 10b and its epimer 11b were synthesized from cyanohydrin benzoates 8a, 9a and cyanohydrin acetates 8b, 9b, respectively, by treatment with hydroxylamine in methanol via intramolecular transacylation and subsequent cyclization of the corresponding amidoximes. Hydrolysis and reduction of the dimethoxymethyl groups in the above compounds gave the desired compounds 12a, 13a, 12b and 13b, (C) 2000 Elsevier Science Ltd. All rights reserved.