tert-butyl (4R)-4-[(2R,3R)-2,3-dihydroxy-4-methoxy-4-oxobutan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 190664-58-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4R)-4-[(2R,3R)-2,3-dihydroxy-4-methoxy-4-oxobutan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 190664-58-5
• 化学式: C₁₅H₂₇NO₇
• 分子量: 333.382
• InChiKey: MSXFCUJTNUCZAH-HFBDOXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-[(2R,3R)-2,3-dihydroxy-4-methoxy-4-oxobutan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 (3R,4R,5R)-5-amino-3,4-dihydroxy-4-methyloxan-2-one
  参考文献：
  名称：

  Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments

  摘要：

  A retrosynthetic analysis (Scheme I) of maduropeptin chromophore artifact I defined compounds 2 and 3 as required building block;. The construction of 2 was achieved starling from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived delta-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00724-7
• 作为产物：
  描述：

  (4S)-4-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 73.0h， 生成 tert-butyl (4R)-4-[(2R,3R)-2,3-dihydroxy-4-methoxy-4-oxobutan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments

  摘要：

  A retrosynthetic analysis (Scheme I) of maduropeptin chromophore artifact I defined compounds 2 and 3 as required building block;. The construction of 2 was achieved starling from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived delta-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00724-7

文献信息

• Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments
  作者：K.C. Nicolaou、Kazunori Koide、Jinyou Xu、Mark H. Izraelewicz

  DOI：10.1016/s0040-4039(97)00724-7

  日期：1997.5

  A retrosynthetic analysis (Scheme I) of maduropeptin chromophore artifact I defined compounds 2 and 3 as required building block;. The construction of 2 was achieved starling from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived delta-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3). (C) 1997 Elsevier Science Ltd.