2-amino-2-deoxyglucitol | 740062-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxyglucitol
• 英文别名: 2-Amino-2-desoxy-D-glucit；(2S,3S,4R,5S)-5-aminohexane-1,2,3,4,6-pentol
• CAS: 740062-88-8
• 化学式: C₆H₁₅NO₅
• 分子量: 181.189
• InChiKey: FQORWEQXRQVPBZ-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-2-deoxyglucitol 、 25,27-bis(methoxycarboxylic acid)-26,28-dihydroxycalix[4]arene 在 2-ethoxy-1,2-dihydroquinoline 、 二异丙胺 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 864.0h， 以48%的产率得到25,27-bis[N-(2,3,4,5-tetrahydroxy-1-hydroxymethyl-pentyl)aminocarbonylmethoxy]-calix[4]arene-26,28-diol
  参考文献：
  名称：

  杯[4]芳烃与未保护的羟胺的缩合反应及其水溶性

  摘要：

  在本报告中，我们描述了一种方便的方法来创建带中性电荷的水溶性杯芳烃[4]芳烃，其中芳烃的下部边缘带有羟基酰胺。使用2-乙氧基-1,2-二氢喹啉作为偶联剂，实现了二元酸杯[4]芳烃与几种未保护的羟胺的选择性酰胺化反应。衍生的杯[4]芳烃的溶解度取决于羟酰胺的结构以及羟基数。水中衍生化合物的分子模拟表明，分子内氢键的形成是溶解度的重要组成部分。含有10个羟基的杯[4]芳烃与含有两个羧酸盐的杯[4]芳烃一样易溶于水。

  DOI：

  10.1016/s0040-4020(01)00965-6
• 作为产物：
  描述：

  5-amino-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 在 三乙基硅烷 作用下， 生成 2-amino-2-deoxyglucitol
  参考文献：
  名称：

  Total syntheses of (+)- and (−)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-d- and l-glucitol) and of (+)- and (−)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-d- and l-iditol) via furoisoxazoline-3-aldehydes

  摘要：

  The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00287-0

文献信息

• Total syntheses of (+)- and (−)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-d- and l-glucitol) and of (+)- and (−)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-d- and l-iditol) via furoisoxazoline-3-aldehydes
  作者：Christophe Schaller、Pierre Vogel、Volker Jäger

  DOI：10.1016/s0008-6215(98)00287-0

  日期：1998.12

  The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Condensation reactions of calix[4]arenes with unprotected hydroxyamines, and their resulting water solubilities
  作者：Inese Smukste、David B Smithrud

  DOI：10.1016/s0040-4020(01)00965-6

  日期：2001.11

  describe a convenient method to create neutrally charged, water soluble calix[4]arenes that contain hydroxyamides attached to their lower rims. Selective amidation reactions of a diacid calix[4]arene with several unprotected hydroxyamines was achieved using 2-ethoxy-1,2-dihydroquinoline as the coupling agent. The solubilities of the derivatized calix[4]arenes depended on the structure of the hydroxyamide

  在本报告中，我们描述了一种方便的方法来创建带中性电荷的水溶性杯芳烃[4]芳烃，其中芳烃的下部边缘带有羟基酰胺。使用2-乙氧基-1,2-二氢喹啉作为偶联剂，实现了二元酸杯[4]芳烃与几种未保护的羟胺的选择性酰胺化反应。衍生的杯[4]芳烃的溶解度取决于羟酰胺的结构以及羟基数。水中衍生化合物的分子模拟表明，分子内氢键的形成是溶解度的重要组成部分。含有10个羟基的杯[4]芳烃与含有两个羧酸盐的杯[4]芳烃一样易溶于水。