(5S)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline | 877463-65-5

• 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: (5S)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline
• 英文别名: (4R)-4-[(5S)-3-(phenylmethoxymethyl)-4,5-dihydro-1,2-oxazol-5-yl]-1,3,2-dioxathiolane 2-oxide
• CAS: 877463-65-5
• 化学式: C₁₃H₁₅NO₅S
• 分子量: 297.332
• InChiKey: PUZNCWJTYIUVLJ-OVNXLKRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 反应 32.0h， 以82%的产率得到(5S)-3-benzyloxymethyl-5-[(4R)-2,2-dioxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline
  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 吡啶 、 氯化亚砜 、 溶剂黄146 、 对苯二异氰酸酯 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 44.0h， 生成 (5S)-3-benzyloxymethyl-5-[(4R)-2-oxo-1,3,2-dioxathiolan-4-yl]-2-isoxazoline
  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.