methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose oxime | 1109290-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose oxime
• 英文别名: (NE)-N-[(2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-ylidene]hydroxylamine
• CAS: 1109290-08-5
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: ZVPSUEFQWUNIMY-PGIYNBTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose oxime 在 三聚氯氰 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以42%的产率得到(2R,3R)-3,8-O-benzylidene-[1,4]oxazepin-4-one
  参考文献：
  名称：

  Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes

  摘要：

  The Beckmann rearrangement is a useful reaction employed to provide access to amides from oxime substrates. Applied to cyclic structures, the Beckmann rearrangement leads to ring expansion and allows access to cyclic lactams. Our investigations focused upon the synthesis of glycoside-derived lactams from oxime precursors. In probing a range of conditions, we observed that 2,4,6-trichloro[1,3,5]triazine (TCT) was an effective and mild promoter of the rearrangement affording pyrano- and heptanoside lactam products with excellent regioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.031
• 作为产物：
  描述：

  methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 7.5h， 以72%的产率得到methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose oxime
  参考文献：
  名称：

  Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes

  摘要：

  The Beckmann rearrangement is a useful reaction employed to provide access to amides from oxime substrates. Applied to cyclic structures, the Beckmann rearrangement leads to ring expansion and allows access to cyclic lactams. Our investigations focused upon the synthesis of glycoside-derived lactams from oxime precursors. In probing a range of conditions, we observed that 2,4,6-trichloro[1,3,5]triazine (TCT) was an effective and mild promoter of the rearrangement affording pyrano- and heptanoside lactam products with excellent regioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.031