(3S,4R,5R)-1-(4-methoxybenzyl)-3-benzyloxy-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-one | 1274850-67-7

• 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: (3S,4R,5R)-1-(4-methoxybenzyl)-3-benzyloxy-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-one
• 英文别名: (3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-1-[(4-methoxyphenyl)methyl]-3-phenylmethoxypyrrolidin-2-one
• CAS: 1274850-67-7
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: GVTGATPCOTYZGY-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-1-(4-methoxybenzyl)-3-benzyloxy-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-one 在 盐酸 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 64.5h， 生成 1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇盐酸盐
  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 、 三乙基硅烷 、 trifluoromethanesulfonic acid 、 三氟化硼乙醚 、 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 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 96.0h， 生成 (3S,4R,5R)-1-(4-methoxybenzyl)-3-benzyloxy-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-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.