(2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2S,4S,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate | 877463-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2S,4S,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate
• 英文别名: [(4R,5S)-4-[[(2S,4S,5R)-4,5-dihydroxy-2-(phenylmethoxymethyl)piperidin-1-ium-1-yl]methyl]-2,2-dimethyl-1,3-dioxan-5-yl] sulfate
• CAS: 877463-76-8
• 化学式: C₂₀H₃₁NO₉S
• 分子量: 461.533
• InChiKey: JRRANIUVJWZCLG-QTMHVTGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2S,4S,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 水 为溶剂， 反应 168.0h， 以73%的产率得到(2S,3R)-1,3-dihydroxy-4-[(2S,4S,5R)-4,5-dihydroxy-2-hydroxymethylpiperidinium-1-yl]butane-2-sulfate
  参考文献：
  名称：

  Synthesis of New Nitrogen Analogues of Salacinol and Deoxynojirimycin and Their Evaluation as Glycosidase Inhibitors

  摘要：

  The synthesis of two enantiomerically pure iminosugars, analogues of 1-L-deoxynojirimycin (L-DNJ) and 1-D-deoxymannojirimycin (DW), was achieved using cyclic sulfate substituted isoxazoline derivatives. The piperidine ring was formed via the reduction of an isoxazoline into an amine which underwent a spontaneous intramolecular cyclization by reaction with the cyclic sulfate moiety. The nucleophilic attack of these two trisubstituted piperidines and morpholine on L- and D-erythritol- 1,3-cyclic sulfates gave six new nitrogen analogues of salacinol. The inhibitory properties of the synthesized salacinol analogues were evaluated on several commercial glycosidases.

  DOI：

  10.1021/jo0517388
• 作为产物：
  描述：

  1-benzyloxy-2-nitroethane 在 palladium on activated charcoal 吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 氯化亚砜 、 硫酸 、 氢气 、 sodium carbonate 、 溶剂黄146 、 对苯二异氰酸酯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 131.0h， 生成 (2S,3R)-1,3-dihydroxy-1,3-O-isopropylidene-4-[(2S,4S,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate
  参考文献：
  名称：

  Synthesis of New Nitrogen Analogues of Salacinol and Deoxynojirimycin and Their Evaluation as Glycosidase Inhibitors

  摘要：

  The synthesis of two enantiomerically pure iminosugars, analogues of 1-L-deoxynojirimycin (L-DNJ) and 1-D-deoxymannojirimycin (DW), was achieved using cyclic sulfate substituted isoxazoline derivatives. The piperidine ring was formed via the reduction of an isoxazoline into an amine which underwent a spontaneous intramolecular cyclization by reaction with the cyclic sulfate moiety. The nucleophilic attack of these two trisubstituted piperidines and morpholine on L- and D-erythritol- 1,3-cyclic sulfates gave six new nitrogen analogues of salacinol. The inhibitory properties of the synthesized salacinol analogues were evaluated on several commercial glycosidases.

  DOI：

  10.1021/jo0517388

文献信息

• Synthesis of New Nitrogen Analogues of Salacinol and Deoxynojirimycin and Their Evaluation as Glycosidase Inhibitors
  作者：Estelle Gallienne、Thierry Gefflaut、Jean Bolte、Marielle Lemaire

  DOI：10.1021/jo0517388

  日期：2006.2.1

  The synthesis of two enantiomerically pure iminosugars, analogues of 1-L-deoxynojirimycin (L-DNJ) and 1-D-deoxymannojirimycin (DW), was achieved using cyclic sulfate substituted isoxazoline derivatives. The piperidine ring was formed via the reduction of an isoxazoline into an amine which underwent a spontaneous intramolecular cyclization by reaction with the cyclic sulfate moiety. The nucleophilic attack of these two trisubstituted piperidines and morpholine on L- and D-erythritol- 1,3-cyclic sulfates gave six new nitrogen analogues of salacinol. The inhibitory properties of the synthesized salacinol analogues were evaluated on several commercial glycosidases.