methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside
• 英文别名: 2-[(4aR,6S,7S,8S,8aS)-7-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]isoindole-1,3-dione
• 化学式: C₂₂H₂₁NO₇
• 分子量: 411.411
• InChiKey: NSSSMSIPMHCQTN-IWFLAOPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside 在 一水合肼 作用下， 反应 2.0h， 以56%的产率得到methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside
  参考文献：
  名称：

  Boat conformations

  摘要：

  Addition of the elements of phthalimide to methyl 2,3-anhydro-4,6-O-benzylidene-alpha -D-mannopyranoside (1) under fusion conditions has yielded methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-alpha -D-altropyranoside (2). The conformation of the pyranose ring of 2 has been shown to be non-chair by H-1 NMR spectroscopy, in contrast to the conformations of related derivatives having smaller substituents at C-3. Molecular dynamics simulations of 2 in explicit chloroform-d solvent have indicated four principal conformational possibilities. Of these, the C-7(5)/S-1(5) chair/skew boat form 2d has the lowest potential energy, and is largely consistent with the observed vicinal H-1-H-1 NMR coupling constants. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00036-2
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 potassium phtalimide 作用下， 反应 0.5h， 以45%的产率得到methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside
  参考文献：
  名称：

  Boat conformations

  摘要：

  Addition of the elements of phthalimide to methyl 2,3-anhydro-4,6-O-benzylidene-alpha -D-mannopyranoside (1) under fusion conditions has yielded methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-alpha -D-altropyranoside (2). The conformation of the pyranose ring of 2 has been shown to be non-chair by H-1 NMR spectroscopy, in contrast to the conformations of related derivatives having smaller substituents at C-3. Molecular dynamics simulations of 2 in explicit chloroform-d solvent have indicated four principal conformational possibilities. Of these, the C-7(5)/S-1(5) chair/skew boat form 2d has the lowest potential energy, and is largely consistent with the observed vicinal H-1-H-1 NMR coupling constants. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00036-2

文献信息

• Boat conformations
  作者：Bruce Coxon、Robert C. Reynolds

  DOI：10.1016/s0008-6215(01)00036-2

  日期：2001.4

  Addition of the elements of phthalimide to methyl 2,3-anhydro-4,6-O-benzylidene-alpha -D-mannopyranoside (1) under fusion conditions has yielded methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-alpha -D-altropyranoside (2). The conformation of the pyranose ring of 2 has been shown to be non-chair by H-1 NMR spectroscopy, in contrast to the conformations of related derivatives having smaller substituents at C-3. Molecular dynamics simulations of 2 in explicit chloroform-d solvent have indicated four principal conformational possibilities. Of these, the C-7(5)/S-1(5) chair/skew boat form 2d has the lowest potential energy, and is largely consistent with the observed vicinal H-1-H-1 NMR coupling constants. (C) 2001 Elsevier Science Ltd. All rights reserved.