(3R,4R,5R)-5-amino-3,4-dihydroxy-4-methyloxan-2-one | 1054615-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4R,5R)-5-amino-3,4-dihydroxy-4-methyloxan-2-one
• CAS: 1054615-62-1
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: YUFDMOWYWXSOSM-ALEPSDHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-5-amino-3,4-dihydroxy-4-methyloxan-2-one 在 N-甲基吗啉 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 生成 3,6-dimethyl-N-[(3R,4R,5R)-4-methyl-6-oxo-4,5-bis(triethylsilyloxy)oxan-3-yl]-2-triethylsilyloxybenzamide
  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 、 camphor-10-sulfonic acid 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 107.0h， 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

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.