N-benzyl-1,4-dideoxy-1,4-imino-L-mannitol | 934716-03-7

• 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: N-benzyl-1,4-dideoxy-1,4-imino-L-mannitol
• 英文别名: (2S,3R,4S)-1-benzyl-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol
• CAS: 934716-03-7
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: GJXFUTMBLXCJRJ-CYDGBPFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-1,4-dideoxy-1,4-imino-L-mannitol 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 19.0h， 以100%的产率得到1,4-dideoxy-1,4-imino-L-mannitol
  参考文献：
  名称：

  Looking glass inhibitors: synthesis of a potent naringinase inhibitor l-DIM [1,4-dideoxy-1,4-imino-l-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-d-mannitol] a potent α-d-mannosidase inhibitor

  摘要：

  The synthesis of L-DIM [1,4-dideoxy-1,4-imino-L-mannitol] and of 1,4-imino-D-glycero-L-talo-heptitol from D-glycero-D-gulyheptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. L-DIM, the enantiomer of the potent alpha-D-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-D-mannitol] is a good inhibitor of naringinase (an alpha-L-rhatimosidase) with a K-i of 3.63 mu M. 1,4-Imino-D-glycero-L-talo-heptitol is a moderate inhibitor of naringinase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.010
• 作为产物：
  描述：

  (3aR,6S,6aR)-6-[(R)-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-diethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium periodate 、 锂硼氢 、 Amberlyst 15 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 148.78h， 生成 N-benzyl-1,4-dideoxy-1,4-imino-L-mannitol
  参考文献：
  名称：

  Looking glass inhibitors: synthesis of a potent naringinase inhibitor l-DIM [1,4-dideoxy-1,4-imino-l-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-d-mannitol] a potent α-d-mannosidase inhibitor

  摘要：

  The synthesis of L-DIM [1,4-dideoxy-1,4-imino-L-mannitol] and of 1,4-imino-D-glycero-L-talo-heptitol from D-glycero-D-gulyheptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. L-DIM, the enantiomer of the potent alpha-D-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-D-mannitol] is a good inhibitor of naringinase (an alpha-L-rhatimosidase) with a K-i of 3.63 mu M. 1,4-Imino-D-glycero-L-talo-heptitol is a moderate inhibitor of naringinase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.010

文献信息

• Looking glass inhibitors: synthesis of a potent naringinase inhibitor l-DIM [1,4-dideoxy-1,4-imino-l-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-d-mannitol] a potent α-d-mannosidase inhibitor
  作者：Anders E. Håkansson、Jeroen van Ameijde、Luisa Guglielmini、Graeme Horne、Robert J. Nash、Emma L. Evinson、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetasy.2007.01.010

  日期：2007.2

  The synthesis of L-DIM [1,4-dideoxy-1,4-imino-L-mannitol] and of 1,4-imino-D-glycero-L-talo-heptitol from D-glycero-D-gulyheptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. L-DIM, the enantiomer of the potent alpha-D-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-D-mannitol] is a good inhibitor of naringinase (an alpha-L-rhatimosidase) with a K-i of 3.63 mu M. 1,4-Imino-D-glycero-L-talo-heptitol is a moderate inhibitor of naringinase. (c) 2007 Elsevier Ltd. All rights reserved.