N-butyl-1-deoxy-L-ido-homonojirimycin | 909249-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-butyl-1-deoxy-L-ido-homonojirimycin
• 英文别名: (2S,3R,4R,5S)-1-butyl-2-(2-hydroxyethyl)piperidine-3,4,5-triol
• CAS: 909249-86-1
• 化学式: C₁₁H₂₃NO₄
• 分子量: 233.308
• InChiKey: FGBCEEFGEBEAEK-UKKRHICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-butyl-1-deoxy-L-ido-homonojirimycin 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以94%的产率得到tetra-O-acetyl-N-butyl-1-deoxy-L-ido-homonojirimycin
  参考文献：
  名称：

  Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin

  摘要：

  Conjugate addition of n-butyl amine to D-glucose derived alpha,beta-unsaturated ester 4 afforded P-amino esters 5a,b that on reduction of ester group,. 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deOXY-D-gluco-homonojirimycin 2c and N-butyl 1-deOXY-L-ido-homonojirimycin 2d which were found to be selective P-glucosidase inhibitors with an IC50 value in millimolar range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.027
• 作为产物：
  描述：

  ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-butylamino)-5,6-dideoxy-β-L-ido-heptofuranuronate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 ammonium formate 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.5h， 生成 N-butyl-1-deoxy-L-ido-homonojirimycin
  参考文献：
  名称：

  Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin

  摘要：

  Conjugate addition of n-butyl amine to D-glucose derived alpha,beta-unsaturated ester 4 afforded P-amino esters 5a,b that on reduction of ester group,. 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deOXY-D-gluco-homonojirimycin 2c and N-butyl 1-deOXY-L-ido-homonojirimycin 2d which were found to be selective P-glucosidase inhibitors with an IC50 value in millimolar range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.027

文献信息

• Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin
  作者：Shankar D. Markad、Narayan S. Karanjule、Tarun Sharma、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2006.04.027

  日期：2006.8

  Conjugate addition of n-butyl amine to D-glucose derived alpha,beta-unsaturated ester 4 afforded P-amino esters 5a,b that on reduction of ester group,. 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deOXY-D-gluco-homonojirimycin 2c and N-butyl 1-deOXY-L-ido-homonojirimycin 2d which were found to be selective P-glucosidase inhibitors with an IC50 value in millimolar range. (c) 2006 Elsevier Ltd. All rights reserved.