2,5-dideoxy-1-O-(6'-hydroxyhexyl)-2,5-imino-D-mannitol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,5-dideoxy-1-O-(6'-hydroxyhexyl)-2,5-imino-D-mannitol
• 英文别名: (2R,3R,4R,5R)-2-(6-hydroxyhexoxymethyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
• 化学式: C₁₂H₂₅NO₅
• 分子量: 263.334
• InChiKey: MSKILGCGDPGKIK-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-溴正己醇 在 palladium dihydroxide Amberlite IR-120 (H+) 、 EC 5.3.1.5 、 glucose isomerase Sweetzyme T 、 氢气 、 sodium hydride 、 magnesium sulfate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 93.0h， 生成 2,5-dideoxy-1-O-(6'-hydroxyhexyl)-2,5-imino-D-mannitol
  参考文献：
  名称：

  Biologically Active 1-Aminodeoxy and 1-O-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol

  摘要：

  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.

  DOI：

  10.1080/07328300008544129

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.