(2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine | 292074-26-1

• 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: (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine
• 英文别名: tert-butyl (2R,3R,4R,5R)-2-ethenyl-5-(methoxymethoxy)-3,4-bis(phenylmethoxy)piperidine-1-carboxylate
• CAS: 292074-26-1
• 化学式: C₂₈H₃₇NO₆
• 分子量: 483.605
• InChiKey: ISLSOPAMSDRYOL-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine 在 palladium on activated charcoal 盐酸 、 氢气 、 臭氧 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-甘露糖野尻霉素盐酸盐
  参考文献：
  名称：

  Palladium(II)-Catalyzed Cyclization of Urethanes and Total Synthesis of 1-Deoxymannojirimycin

  摘要：

  [GRAPHICS]The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation, The cycloadduct 9 was converted to 1-deoxymannojirimycin.

  DOI：

  10.1021/ol0060432
• 作为产物：
  描述：

  (2R,3S,4R)-3,4-dibenzyloxy-2-methoxymethyloxy-7-pivaloyloxy-5-heptenamine 在 双(乙腈)氯化钯(II) 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine
  参考文献：
  名称：

  Palladium(II)-Catalyzed Cyclization of Urethanes and Total Synthesis of 1-Deoxymannojirimycin

  摘要：

  [GRAPHICS]The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation, The cycloadduct 9 was converted to 1-deoxymannojirimycin.

  DOI：

  10.1021/ol0060432

文献信息

• Palladium(II)-Catalyzed Cyclization of Urethanes and Total Synthesis of 1-Deoxymannojirimycin
  作者：Hajime Yokoyama、Kumiko Otaya、Hisatake Kobayashi、Masahiro Miyazawa、Seiji Yamaguchi、Yoshiro Hirai

  DOI：10.1021/ol0060432

  日期：2000.8.1

  [GRAPHICS]The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation, The cycloadduct 9 was converted to 1-deoxymannojirimycin.