(2S,4S,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate | 877463-69-9

• 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,4S,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate
• 英文别名: [(3R,4S,6S)-4-hydroxy-6-(phenylmethoxymethyl)piperidin-1-ium-3-yl] sulfate
• CAS: 877463-69-9
• 化学式: C₁₃H₁₉NO₆S
• 分子量: 317.363
• InChiKey: REQUXIQTCIXKAB-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate 在 硫酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 56.0h， 生成 (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-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
• 作为产物：
  描述：

  1-benzyloxy-2-nitroethane 在 palladium on activated charcoal 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 Amberlyst^R 15 、 氢气 、 sodium carbonate 、 对苯二异氰酸酯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 119.0h， 生成 (2S,4S,5R)-3-benzyloxymethyl-4-hydroxypiperidinium 5-sulfate
  参考文献：
  名称：

  首次通过氢解立体控制还原异恶唑啉：通过环状硫酸盐制备亚氨基糖的新途径

  摘要：

  使用环状硫酸盐取代的异恶唑啉衍生物合成了四种新的三羟基哌啶，被认为是 1-脱氧野尻霉素 (DNJ) 和 1-脱氧甘露尻霉素 (DMJ) 的类似物。关键步骤是将异恶唑啉一锅还原为胺，该胺以高立体选择性和区域选择性对硫酸酯进行分子内攻击。异恶唑啉前体是通过 2,2-二甲基-4-乙烯基-1,3-二氧戊环和 1-苄氧基-2-硝基乙烷之间的 1,3-双极环加成反应获得的。

  DOI：

  10.1055/s-2002-32967

文献信息

• First Stereocontrolled Reduction of Isoxazoline by Hydrogenolysis: A New Route to Iminosugars via Cyclic Sulfates
  作者：Marielle Lemaire、Nicolas Veny、Thierry Gefflaut、Estelle Gallienne、Robert Chênevert、Jean Bolte

  DOI：10.1055/s-2002-32967

  日期：——

  The synthesis of four new trihydroxylated piperidines, considered as analogues of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ), was achieved using cyclic sulfate substituted isoxazoline derivatives. The key step is the one-pot reduction of an isoxazoline to an amine which undergoes intramolecular attack on the sulfate ester with high stereoselectivity and regioselectivity. The isoxazoline

  使用环状硫酸盐取代的异恶唑啉衍生物合成了四种新的三羟基哌啶，被认为是 1-脱氧野尻霉素 (DNJ) 和 1-脱氧甘露尻霉素 (DMJ) 的类似物。关键步骤是将异恶唑啉一锅还原为胺，该胺以高立体选择性和区域选择性对硫酸酯进行分子内攻击。异恶唑啉前体是通过 2,2-二甲基-4-乙烯基-1,3-二氧戊环和 1-苄氧基-2-硝基乙烷之间的 1,3-双极环加成反应获得的。
• 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.