3,5,6-tri-O-pivaloyl-1-deoxy-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one | 285568-32-3

• 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: 3,5,6-tri-O-pivaloyl-1-deoxy-α-D-glucofurano[1,2-d]-1',3'-oxazolidin-2'-one
• 英文别名: [(2R)-2-[(3aS,5R,6S,6aR)-6-(2,2-dimethylpropanoyloxy)-2-oxo-3a,5,6,6a-tetrahydro-3H-furo[2,3-d][1,3]oxazol-5-yl]-2-(2,2-dimethylpropanoyloxy)ethyl] 2,2-dimethylpropanoate
• CAS: 285568-32-3
• 化学式: C₂₂H₃₅NO₉
• 分子量: 457.521
• InChiKey: GJTKXZDMDOIYPB-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,5,6-tri-O-pivaloyl-1-deoxy-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 2.83h， 生成 [(2R)-2-[(3aS,5R,6S,6aR)-6-(2,2-dimethylpropanoyloxy)-3-[(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl]-2-oxo-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]oxazol-5-yl]-2-(2,2-dimethylpropanoyloxy)ethyl] 2,2-dimethylpropanoate
  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：

  α-D-glucofurano<1,2-d>oxazolidin-2-one 、 三甲基乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以73%的产率得到3,5,6-tri-O-pivaloyl-1-deoxy-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.