5-azido-5-deoxy-1,2-O-isopropylidene-3-O-(methoxymethyl)-α-D-glucofuranose | 192806-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-1,2-O-isopropylidene-3-O-(methoxymethyl)-α-D-glucofuranose
• 英文别名: 5-azido-5-deoxy-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose
• CAS: 192806-38-5
• 化学式: C₁₁H₁₉N₃O₆
• 分子量: 289.288
• InChiKey: NJKDXABEEKHPLU-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115.14
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-3-O-(methoxymethyl)-α-D-glucofuranose 在 Amberlite IR 120 ⁽¹⁺⁾-form 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 5-azido-5-deoxy-6-O-hexyl-α-D-glucofuranose
  参考文献：
  名称：

  Probing the aglycon binding site of a β-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-d-mannitol derivatives and their structure–activity relationships as competitive inhibitors

  摘要：

  A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. K-i values are compared with those of previously prepared close relatives. Findings suggest dramatic effects exerted by the aglycon binding site on substrate/ inhibitor binding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.037
• 作为产物：
  描述：

  5-azido-5-deoxy-6-O-dimethyl(1,1,2-trimethylpropyl)silyl-1,2-O-isopropylidene-α-D-glucofuranose 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-3-O-(methoxymethyl)-α-D-glucofuranose
  参考文献：
  名称：

  Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol: Syntheses and glucosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-d-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-d-mannitol

  摘要：

  1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannit and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconversion reactions as the key steps of the syntheses. Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00099-2

文献信息

• Biologically Active 1-Aminodeoxy and 1-<i>O</i>-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol
  作者：Tanja M. Wrodnigg、Walter Gaderbauer、Peter Greimel、Herwig Häusler、Friedrich K. (Fitz) Sprenger、Arnold E. Stütz、Chris Virgona、Stephen G. Withers

  DOI：10.1080/07328300008544129

  日期：2000.1.1

  By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-(N,N-dibenzyl)amino-1,5-dideoxy-D-fructopyranose 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and in excellent overall yield. Likewise, other amines were employed to introduce extended side chains ultimately suitable for attachment of the inhibitor to solid supports. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to I-amino deoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. A range of selected chain extended analogues was prepared by acylation of N-1. Inhibitors obtained exhibit K-i-values with D-glucosidases in the micromolar range. Interestingly, 1-N-acylation resulted in superior inhibitory activities, as did the addition of a hexyl chain.