methyl (2R,3S,7R,7aS)-7-methoxy-2,7,7a-trimethyl-5-oxo-2H-oxazolo[4,3-b]oxazole-3-carboxylate | 1139694-87-3

• 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: methyl (2R,3S,7R,7aS)-7-methoxy-2,7,7a-trimethyl-5-oxo-2H-oxazolo[4,3-b]oxazole-3-carboxylate
• 英文别名: methyl (2R,3S,7R,7aS)-7-methoxy-2,7,7a-trimethyl-5-oxo-2,3-dihydro-[1,3]oxazolo[3,2-c][1,3]oxazole-3-carboxylate
• CAS: 1139694-87-3
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: YAWHBTLSPKBFLT-GJOTXNKNSA-N

物化性质

• 沸点：
  383.3±42.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S,7R,7aS)-7-methoxy-2,7,7a-trimethyl-5-oxo-2H-oxazolo[4,3-b]oxazole-3-carboxylate 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到methyl (Z)-2-[(4S,5R)-4-hydroxy-5-methoxy-4,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]but-2-enoate
  参考文献：
  名称：

  α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

  摘要：

  The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.031
• 作为产物：
  描述：

  BOC-苏氨酸甲酯 、 2,2,3,3-四甲氧基丁烷 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以69%的产率得到methyl (2R,3S,7R,7aS)-7-methoxy-2,7,7a-trimethyl-5-oxo-2H-oxazolo[4,3-b]oxazole-3-carboxylate
  参考文献：
  名称：

  α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

  摘要：

  The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.031

文献信息

• α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine
  作者：Carlos Aydillo、Alberto Avenoza、Jesús H. Busto、Gonzalo Jiménez-Osés、Jesús M. Peregrina、María M. Zurbano

  DOI：10.1016/j.tetasy.2008.11.031

  日期：2008.12

  The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.