5-(氨基甲基)-1,2-噁唑烷-3-酮 | 141267-47-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 5-(氨基甲基)-1,2-噁唑烷-3-酮
• 中文别名: (3S,4S,5R)-7-(2,4-二氯苯基)-3,4,5-三羟基庚酸钠
• 英文名称: Sodium 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-D-xylo-heptonate
• 英文别名: 2,6,7-Trideoxy-7-C-(2,4-dichlorophenyl)heptonic acid；sodium;(3S,4S,5R)-7-(2,4-dichlorophenyl)-3,4,5-trihydroxyheptanoate
• CAS: 141267-47-2
• 化学式: C₁₃H₁₅Cl₂O₅*Na
• 分子量: 345.155
• InChiKey: WJTBMLZWEDIMFJ-CHZGQIEOSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.85
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,6-Dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 氢气 、 双氧水 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 、 乙酸乙酯 、 苯 为溶剂， 反应 146.5h， 生成 5-(氨基甲基)-1,2-噁唑烷-3-酮
  参考文献：
  名称：

  Synthesis of 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-d-xylo-heptonic acid and 6-(2,4-dichlorophenyl)-d-xylo-2,3,4-trihydroxyhexanesulfonic acid

  摘要：

  2,4-O-Benzylidene-L-xylose was converted via a Wittig reaction into Z-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol (17), which, on hydrogenation, gave 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol (33). tert-Butyldimethylsililation of the primary hydroxyl group of 33, followed by 4-methoxybenzylation, and desilylation afforded 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-2,3,4-tri-O-(4-methoxybenzyl)-D-xylo-hexitol (54). A Mitsunobu-type reaction of 54 replaced HO-1 by cyanide to give, after hydrolysis and hydrogenolysis, 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-D-xylo-heptono-1,4-lactone (55). Mesylation of 33 and then acetylation gave 2,3,4-tri-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-1-O-methanesulfonyl-D-xylo-hexitol (63), which was converted via its 1-thiobenzoate into bis[1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol] 1,1'-disulfide (65). Acetylation of 65, followed by permanganate oxidation and deacetylation, afforded sodium 6-(2,4-dichlorophenyl)-D-xylo-2,3,4-trihydroxy-hexanesulfonate (67). Both 57 (obtained from 55 by hydrolysis with NaOH) and 67 are weak inhibitors of HMG-CoA reductase.

  DOI：

  10.1016/s0008-6215(00)90499-3

文献信息

• Synthesis of 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-d-xylo-heptonic acid and 6-(2,4-dichlorophenyl)-d-xylo-2,3,4-trihydroxyhexanesulfonic acid
  作者：János Kuszmann、Benjamin Podányi

  DOI：10.1016/s0008-6215(00)90499-3

  日期：1992.3

  2,4-O-Benzylidene-L-xylose was converted via a Wittig reaction into Z-2,4-O-benzylidene-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hex-5-enitol (17), which, on hydrogenation, gave 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol (33). tert-Butyldimethylsililation of the primary hydroxyl group of 33, followed by 4-methoxybenzylation, and desilylation afforded 5,6-dideoxy-6-C-(2,4-dichlorophenyl)-2,3,4-tri-O-(4-methoxybenzyl)-D-xylo-hexitol (54). A Mitsunobu-type reaction of 54 replaced HO-1 by cyanide to give, after hydrolysis and hydrogenolysis, 2,6,7-trideoxy-7-C-(2,4-dichlorophenyl)-D-xylo-heptono-1,4-lactone (55). Mesylation of 33 and then acetylation gave 2,3,4-tri-O-acetyl-5,6-dideoxy-6-C-(2,4-dichlorophenyl)-1-O-methanesulfonyl-D-xylo-hexitol (63), which was converted via its 1-thiobenzoate into bis[1,5,6-trideoxy-6-C-(2,4-dichlorophenyl)-D-xylo-hexitol] 1,1'-disulfide (65). Acetylation of 65, followed by permanganate oxidation and deacetylation, afforded sodium 6-(2,4-dichlorophenyl)-D-xylo-2,3,4-trihydroxy-hexanesulfonate (67). Both 57 (obtained from 55 by hydrolysis with NaOH) and 67 are weak inhibitors of HMG-CoA reductase.