ethyl (6S)-3-O-benzyl-6-deoxy-6-(N-benzylaminomethyl)-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanoate | 1225441-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (6S)-3-O-benzyl-6-deoxy-6-(N-benzylaminomethyl)-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanoate
• 英文别名: ethyl (2S,3R)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[(benzylamino)methyl]-3-hydroxypropanoate
• CAS: 1225441-89-3
• 化学式: C₂₇H₃₅NO₇
• 分子量: 485.577
• InChiKey: HMVJJKDNQZXGEI-XSGWZPFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (6S)-3-O-benzyl-6-deoxy-6-(N-benzylaminomethyl)-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以67%的产率得到(6R)-3-O-benzyl-6-deoxy-6-(N-benzylaminomethyl)-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanose
  参考文献：
  名称：

  Synthesis of eight-membered iminocyclitols from d-glucose

  摘要：

  The Baylis-Hillman reaction of 3-o-benzyl-alpha-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated alpha-methylene-beta-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.044
• 作为产物：
  描述：

  ethyl 3-O-benzyl-6-deoxy-6-methylene-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanoate 、 苄胺 反应 6.0h， 以88.7%的产率得到ethyl (6S)-3-O-benzyl-6-deoxy-6-(N-benzylaminomethyl)-1,2-O-isopropylidene-α-D-gluco-1,4-hepto-furanoate
  参考文献：
  名称：

  Synthesis of eight-membered iminocyclitols from d-glucose

  摘要：

  The Baylis-Hillman reaction of 3-o-benzyl-alpha-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated alpha-methylene-beta-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.044

文献信息

• Synthesis of eight-membered iminocyclitols from d-glucose
  作者：Vrushali H. Jadhav、Omprakash P. Bande、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tet.2010.02.044

  日期：2010.4

  The Baylis-Hillman reaction of 3-o-benzyl-alpha-d-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated alpha-methylene-beta-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield. (C) 2010 Elsevier Ltd. All rights reserved.