(1S,2S,3R)-1,2-di-O-acetyl-3-methylcyclohex-5-ene-1,2-diol | 432547-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,3R)-1,2-di-O-acetyl-3-methylcyclohex-5-ene-1,2-diol
• 英文别名: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-5a-carba-L-arabino-hex-1-enitol
• CAS: 432547-06-3
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: HPUAASJIYBEFAV-GGVZMXCHSA-N

物化性质

• 沸点：
  259.5±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-1,2-di-O-acetyl-3-methylcyclohex-5-ene-1,2-diol 在 吡啶 、 disodium hydrogenphosphate 、 disodium hydrogenphosphate 、 sodium methylate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 200.0h， 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：

  3-环己烯-1,2-二醇,6-(溴甲基)-,二乙酸酯,(1S,2S,6R)- 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以86%的产率得到(1S,2S,3R)-1,2-di-O-acetyl-3-methylcyclohex-5-ene-1,2-diol
  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

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.