methyl (Z)-2-[(4S,5R)-4-hydroxy-5-methoxy-4,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]but-2-enoate | 1139694-91-9

• 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 (Z)-2-[(4S,5R)-4-hydroxy-5-methoxy-4,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]but-2-enoate
• CAS: 1139694-91-9
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: BBIXFGPGZQPUFX-QIAMSNJGSA-N

物化性质

• 沸点：
  344.8±52.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-[(4S,5R)-4-hydroxy-5-methoxy-4,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]but-2-enoate 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 、 重水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到(Z)-methyl 2-((4'S,5'R)-4'-hydroxy-5'-methoxy-4',5'-dimethyl-2'-oxooxazolidin-3-yl)4-deuteriumbut-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：

  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

文献信息

• A Biomimetic Approach to Lanthionines
  作者：Carlos Aydillo、Alberto Avenoza、Jesús H. Busto、Gonzalo Jiménez-Osés、Jesús M. Peregrina、María M. Zurbano

  DOI：10.1021/ol203068s

  日期：2012.1.6

  The asymmetric sulfa-Michael additions of appropriately protected l- and d-cysteine derivatives to new chiral dehydroamino acid derivatives have been developed as key steps in the synthesis of biologically important cysteine derivatives, such as lanthionine (Lan) and β-methyllanthionine (MeLan), which are unusual bis-α-amino acids found in the emerging lantibiotics such as nisin.

  已开发出在新的手性脱氢氨基酸衍生物中适当保护的l和d-半胱氨酸衍生物的不对称磺胺-迈克尔加成反应，是合成重要的半胱氨酸衍生物（例如羊毛硫氨酸（Lan）和β-甲基羊毛硫氨酸（MeLan））中的关键步骤。 ，这是新兴的羊毛硫抗生素（如乳链菌肽）中发现的不常见的双α-氨基酸。
• 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.