1,5-anhydro-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol | 432547-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol
• 英文别名: (1S,2R,3R)-3-methylcyclohex-5-ene-1,2-diol；(1R,2S,6R)-6-methylcyclohex-3-ene-1,2-diol
• CAS: 432547-08-5
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: OPLKTKYNMNKXMA-DSYKOEDSSA-N

物化性质

• 沸点：
  207.6±40.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol 在 disodium hydrogenphosphate 、 disodium hydrogenphosphate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 149.0h， 生成
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023
• 作为产物：
  描述：

  (1S,2S,3R)-1,2-di-O-acetyl-3-methylcyclohex-5-ene-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 苯甲醇钠 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,5-anhydro-2,6-dideoxy-5a-carba-L-lyxo-hex-1-enitol
  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