(9S,12S,15S)-4-benzyloxy-15-dibenzylamino-12-(4-hydroxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid benzyl ester | 903523-86-4

• 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: (9S,12S,15S)-4-benzyloxy-15-dibenzylamino-12-(4-hydroxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid benzyl ester
• 英文别名: benzyl (9S,12S,15S)-15-(dibenzylamino)-12-[(4-hydroxyphenyl)methyl]-11,14-dioxo-4-phenylmethoxy-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-9-carboxylate
• CAS: 903523-86-4
• 化学式: C₅₅H₅₁N₃O₇
• 分子量: 866.026
• InChiKey: XKVDVLLAHBABBK-HJENIEFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  65
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (9S,12S,15S)-4-benzyloxy-15-dibenzylamino-12-(4-hydroxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid benzyl ester 、 乙酸酐 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以50%的产率得到K-13
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine benzyl ester 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 二苯基磷酸 、 碳酸氢钠 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.5h， 生成 (9S,12S,15S)-4-benzyloxy-15-dibenzylamino-12-(4-hydroxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid benzyl ester
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960

文献信息

• Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives
  作者：Qian Cai、Gang He、Dawei Ma

  DOI：10.1021/jo0606960

  日期：2006.7.1

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.