(4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-2,2-dimethyl-5-nonyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one | 1274850-33-7

• 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: (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-2,2-dimethyl-5-nonyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one
• 英文别名: (4aR,7S,7aS)-4a-hydroxy-2,2-dimethyl-5-nonyl-7-phenylmethoxy-7,7a-dihydro-4H-[1,3]dioxino[5,4-b]pyrrol-6-one
• CAS: 1274850-33-7
• 化学式: C₂₄H₃₇NO₅
• 分子量: 419.561
• InChiKey: IGQSBHIJXHOLQX-AWRGLXIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-2,2-dimethyl-5-nonyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以94%的产率得到(4aS,7R,7aR)-7-benzyloxyhexahydro-2,2-dimethyl-5-nonyl[1,3]dioxino[5,4-b]pyrrole
  参考文献：
  名称：

  A Versatile Approach to N-Alkylated 1,4-Dideoxy-1,4-imino-d-arabinitols and 1,4-Dideoxy-1,4-imino-l-xylitols

  摘要：

  A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.

  DOI：

  10.1021/jo1020322
• 作为产物：
  描述：

  methyl-1,3-di-O-isopropylidene-α-D-fructofuranoside 在 咪唑 、 碘 、 sodium hydride 、 对甲苯磺酸 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.25h， 生成 (4aR,7S,7aS)-7-benzyloxytetrahydro-4a-hydroxy-2,2-dimethyl-5-nonyl[1,3]dioxino[5,4-b]pyrrol-6(4H)-one
  参考文献：
  名称：

  A Versatile Approach to N-Alkylated 1,4-Dideoxy-1,4-imino-d-arabinitols and 1,4-Dideoxy-1,4-imino-l-xylitols

  摘要：

  A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.

  DOI：

  10.1021/jo1020322

文献信息

• A Versatile Approach to <i>N</i>-Alkylated 1,4-Dideoxy-1,4-imino-<scp>d</scp>-arabinitols and 1,4-Dideoxy-1,4-imino-<scp>l</scp>-xylitols
  作者：Guan-Nan Wang、Lin Yang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/jo1020322

  日期：2011.4.1

  A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.