(5R)-3-benzyloxymethyl-5-[(1R)-1,2-dihydroxyethyl]-2-isoxazoline | 334999-23-4

• 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: (5R)-3-benzyloxymethyl-5-[(1R)-1,2-dihydroxyethyl]-2-isoxazoline
• 英文别名: (5R)-5-[(1R)-1,2-dihydroxyethyl]-3-benzyloxymethyl-4,5-dihydrooxazole；(1R)-1-[(5R)-3-(phenylmethoxymethyl)-4,5-dihydro-1,2-oxazol-5-yl]ethane-1,2-diol
• CAS: 334999-23-4
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: PUADUSUYEVRPQK-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R)-3-benzyloxymethyl-5-[(1R)-1,2-dihydroxyethyl]-2-isoxazoline 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.83h， 生成 (5R)-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 Aspergillus niger 、 异氰酸苯酯 、 三乙胺 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 48.0h， 生成 (5R)-3-benzyloxymethyl-5-[(1R)-1,2-dihydroxyethyl]-2-isoxazoline
  参考文献：
  名称：

  通过微生物还原5-酰基-异唑啉的脱氧糖：在合成3-脱氧-D-果糖及其衍生物中的应用。

  摘要：

  通过乙酰氧基甲基乙烯基酮和硝基前体的1，3-偶极环加成获得5-酰基恶唑啉3a-d。通过黑曲霉将化合物3a-d生物转化为5-二羟乙基异恶唑啉（+）-4a-d（反）和（-）-5a-d（正）的1：1立体异构体混合物。两种立体异构体均以高收率和高光学纯度获得。由黑曲霉（Aspergillus niger）还原羰基可产生R-构型的醇，从而获得D-糖类似物：化合物（+）-4d被转化为3-deoxy-D-赤-己糖和几种受保护的衍生物。还分两步完成了3-脱氧-D-果糖6-磷酸的全合成，从（+）-4d的总收率达到64％。

  DOI：

  10.1021/jo001480f

文献信息

• Deoxysugars via Microbial Reduction of 5-Acyl-isoxazolines: Application to the Synthesis of 3-Deoxy-<scp>d</scp>-fructose and Derivatives
  作者：Thierry Gefflaut、Christel Martin、Suzy Delor、Pascale Besse、Henri Veschambre、Jean Bolte

  DOI：10.1021/jo001480f

  日期：2001.4.1

  (-)-5a-d (syn). Both stereomers were obtained in good yields and with high optical purities. Carbonyl reduction by Aspergillus niger produces alcohols of R-configuration thus giving an access to D-sugar analogues: Compound (+)-4d was converted to 3-deoxy-D-erythro-hexulose and several protected derivatives. Total synthesis of 3-deoxy-D-fructose-6-phosphate was also achieved in two steps and 64% overall

  通过乙酰氧基甲基乙烯基酮和硝基前体的1，3-偶极环加成获得5-酰基恶唑啉3a-d。通过黑曲霉将化合物3a-d生物转化为5-二羟乙基异恶唑啉（+）-4a-d（反）和（-）-5a-d（正）的1：1立体异构体混合物。两种立体异构体均以高收率和高光学纯度获得。由黑曲霉（Aspergillus niger）还原羰基可产生R-构型的醇，从而获得D-糖类似物：化合物（+）-4d被转化为3-deoxy-D-赤-己糖和几种受保护的衍生物。还分两步完成了3-脱氧-D-果糖6-磷酸的全合成，从（+）-4d的总收率达到64％。
• 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.