(4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene | 292074-23-8

• 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: (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene
• 英文别名: [(E,4R,5S,6R)-7-azido-6-(methoxymethoxy)-4,5-bis(phenylmethoxy)hept-2-enyl] 2,2-dimethylpropanoate
• CAS: 292074-23-8
• 化学式: C₂₈H₃₇N₃O₆
• 分子量: 511.618
• InChiKey: ZXDLOTKUOHWKBA-NTYPAJDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 在 双(乙腈)氯化钯(II) 、 palladium on activated charcoal 盐酸 、 水 、 氢气 、 臭氧 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 70.0h， 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,3R,4R)-3,4-dibenzyloxy-7-pivaloyloxy-5-heptene-1,2-diol 在 15-冠醚-5 sodium azide 、 potassium carbonate 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene
  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.