(1R,2R,3R,4R,6R)-4-methyl-2,3-bis(phenylmethoxy)-7-oxabicyclo[4.1.0]heptane | 432547-10-9

• 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: (1R,2R,3R,4R,6R)-4-methyl-2,3-bis(phenylmethoxy)-7-oxabicyclo[4.1.0]heptane
• CAS: 432547-10-9
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: DIPQJHHWHUGYOE-RMLALMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,4R,6R)-4-methyl-2,3-bis(phenylmethoxy)-7-oxabicyclo[4.1.0]heptane 在 palladium on activated charcoal 盐酸 、 sodium azide 、 15-冠醚-5 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 5a-carba-β-L-fucopyranosylamine
  参考文献：
  名称：

  Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives

  摘要：

  Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine (1) led to preparation of its beta-anomer 4 and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines (5 and 6), in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound 4 was demonstrated to be a potent inhibitor (K-i = 2.0 x 10 (7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent 1. Interestingly, 5 and 6 were found to be rather weak inhibitors. contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors. a-glucose-type validamine and valienamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00004-5
• 作为产物：
  描述：

  3-O-benzoyl-1,5-anhydro-2,6-dideoxy-4-O-mesyl-5a-carba-DL-arabino-hex-1-enitol 在 苯甲醇钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2R,3R,4R,6R)-4-methyl-2,3-bis(phenylmethoxy)-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives

  摘要：

  Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine (1) led to preparation of its beta-anomer 4 and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines (5 and 6), in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound 4 was demonstrated to be a potent inhibitor (K-i = 2.0 x 10 (7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent 1. Interestingly, 5 and 6 were found to be rather weak inhibitors. contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors. a-glucose-type validamine and valienamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00004-5

文献信息

• Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives
  作者：Seiichiro Ogawa、Maiko Watanabe、Ayako Maruyama、Seiichi Hisamatsu

  DOI：10.1016/s0960-894x(02)00004-5

  日期：2002.3

  Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine (1) led to preparation of its beta-anomer 4 and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines (5 and 6), in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound 4 was demonstrated to be a potent inhibitor (K-i = 2.0 x 10 (7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent 1. Interestingly, 5 and 6 were found to be rather weak inhibitors. contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors. a-glucose-type validamine and valienamine. (C) 2002 Elsevier Science Ltd. All rights reserved.