(3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]deca-6,9-dien-2,8-dione | 333999-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]deca-6,9-dien-2,8-dione
• 英文别名: [(2S)-2-[(3S)-3-[acetyl-(4-methylphenyl)sulfonylamino]-2,8-dioxo-1-azaspiro[4.5]deca-6,9-dien-1-yl]-3-(4-methoxyphenyl)propyl] acetate
• CAS: 333999-52-3
• 化学式: C₃₀H₃₂N₂O₈S
• 分子量: 580.659
• InChiKey: CGHQLFNAMPNFEL-CUBQBAPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]deca-6,9-dien-2,8-dione 在 platinum(IV) oxide 、 四丙基高钌酸铵 、 4 A molecular sieve 、 水 、 氢气 、 sodium methylate 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.75h， 生成 (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione
  参考文献：
  名称：

  Total Synthesis of Tricyclic Azaspirane Derivatives of Tyrosine:  FR901483 and TAN1251C

  摘要：

  A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

  DOI：

  10.1021/ja016030z
• 作为产物：
  描述：

  L-酪氨酸乙酯盐酸盐 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 2,2,2-三氟乙醇 、 碘苯二乙酸 、 sodium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 、 氯仿 、 乙腈 为溶剂， 反应 31.0h， 生成 (3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]deca-6,9-dien-2,8-dione
  参考文献：
  名称：

  Total Synthesis of Tricyclic Azaspirane Derivatives of Tyrosine:  FR901483 and TAN1251C

  摘要：

  A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

  DOI：

  10.1021/ja016030z

文献信息

• Total Synthesis of FR901483
  作者：Malika Ousmer、Norbert A. Braun、Marco A. Ciufolini

  DOI：10.1021/ol015526i

  日期：2001.3.1

  [GRAPHICS]The total synthesis of FR901483, a structurally novel immunosuppressant, has been accomplished by the use of technology recently developed in this laboratory for the oxidative cyclization of phenolic oxazolines to spirolactams. Our approach may reflect the biosynthetic pathway leading to the natural product.
• Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols
  作者：Marco A. Ciufolini、Sylvain Canesi、Malika Ousmer、Norbert A. Braun

  DOI：10.1016/j.tet.2006.01.111

  日期：2006.5

  We describe the development of a technique for the oxidative conversion of 4-alkyl phenols to derivatives of the corresponding 4-alkyl-4-amino-2,5-cyclohexanediones. This transformation, which was inspired by biogenetic considerations, constitutes a key step in the total syntheses of FR-901483, TAN-1251C, and cylindricine C. (c) 2006 Elsevier Ltd. All rights reserved.