1,5-anhydro-2,6-dideoxy-3-C-methyl-4-O-methyl-L-arabino-hex-1-enitol | 532392-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,6-dideoxy-3-C-methyl-4-O-methyl-L-arabino-hex-1-enitol
• 英文别名: (2S,3S,4S)-3-methoxy-2,4-dimethyl-2,3-dihydropyran-4-ol
• CAS: 532392-39-5
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HPHQGBSLRYOOMK-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,6-dideoxy-3-C-methyl-4-O-methyl-L-arabino-hex-1-enitol 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 以100%的产率得到1,2-anhydro-6-deoxy-3-C-methyl-4-O-methyl-β-L-mannopyranose
  参考文献：
  名称：

  Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale

  摘要：

  This paper describes the synthesis of C-3 methyl-branched glycosides by epoxidation of partially unblocked L-configured glycals. The stereochemical result depends on the orientation of the allylic hydroxyl group. A theoretical explanation is presented, based on the conformational preferences of the respective glycal half-chair conformations that were estimated by applying the BP density functional and a valence triple-zeta basis set. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00406-8
• 作为产物：
  描述：

  L-olivomycal 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以30%的产率得到1,5-anhydro-2,6-dideoxy-3-C-methyl-4-O-methyl-L-arabino-hex-1-enitol
  参考文献：
  名称：

  Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale

  摘要：

  This paper describes the synthesis of C-3 methyl-branched glycosides by epoxidation of partially unblocked L-configured glycals. The stereochemical result depends on the orientation of the allylic hydroxyl group. A theoretical explanation is presented, based on the conformational preferences of the respective glycal half-chair conformations that were estimated by applying the BP density functional and a valence triple-zeta basis set. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00406-8

文献信息

• Epoxidation of C-branched glycals: unexpected stereochemical results and their theoretical rationale
  作者：Christiane Ernst、Manuel Piacenza、Stefan Grimme、Werner Klaffke

  DOI：10.1016/s0008-6215(02)00406-8

  日期：2003.1

  This paper describes the synthesis of C-3 methyl-branched glycosides by epoxidation of partially unblocked L-configured glycals. The stereochemical result depends on the orientation of the allylic hydroxyl group. A theoretical explanation is presented, based on the conformational preferences of the respective glycal half-chair conformations that were estimated by applying the BP density functional and a valence triple-zeta basis set. (C) 2002 Elsevier Science Ltd. All rights reserved.