3,5,6-tri-O-methyl-1-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one | 285568-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3,5,6-tri-O-methyl-1-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one
• 英文别名: (3aS,5R,6S,6aR)-5-[(1R)-1,2-dimethoxyethyl]-6-methoxy-3a,5,6,6a-tetrahydro-3H-furo[2,3-d][1,3]oxazol-2-one
• CAS: 285568-31-2
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: UJWVTUXMKQHJEC-ZEBDFXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5,6-tri-O-methyl-1-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one 在 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions

  摘要：

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00503-0
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium hydroxide 、 sodium dihydrogenphosphate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 3,5,6-tri-O-methyl-1-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one
  参考文献：
  名称：

  New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions

  摘要：

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00503-0

文献信息

• New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions
  作者：Michael Stöver、Arne Lützen、Peter Köll

  DOI：10.1016/s0957-4166(99)00503-0

  日期：2000.2

  Two new chiral glyco-oxazolidin-2-one auxiliaries based on D-glucose are described. Some N-acyl derivatives were synthesized and used in dialkylboron-mediated asymmetric aldol reactions. All reactions delivered as the major diastereomer those predicted by the Zimmerman-Traxler model and were separated by column chromatography and mostly isolated in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.