¹--D-serine>⁸-cyclosporin | 169690-88-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ¹--D-serine>⁸-cyclosporin
• 英文别名: propan-2-yl 2-[[(2R,5S,8S,11S,14S,17S,23S,26S,29S,32S)-14-[(E,1R,2R)-1-acetyloxy-6-azido-2-methylhex-4-enyl]-17-ethyl-4,7,10,13,19,22,28,32-octamethyl-5,8,23,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-11,26-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacont-2-yl]methoxy]acetate
• CAS: 169690-88-4
• 化学式: C₆₉H₁₂₀N₁₄O₁₆
• 分子量: 1401.8
• InChiKey: WPDFAVMFOPEGHC-ULOLUFDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  99
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  335
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ¹--D-serine>⁸-cyclosporin 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 sodium methylate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 <η-Amino-MeBmt>¹-⁸-cyclosporin lactam
  参考文献：
  名称：

  Bridged Cyclosporins

  摘要：

  The primary hydroxyl group of [D-serine](8)-cyclosporin (1b) was alkylated with isopropyl bromoacetate to provide the O-alkylated compound Ic. Then the secondary hydroxyl group was acetylated to give Id. The allylic methyl group of the MeBmt was brominated giving le. Bromide le was converted to the azide If. Transesterification of the isopropyl ester If to the methyl ester Ig and subsequent hydrolysis provided acid Ih. Reduction of the azide gave the amino acid ii. The bromide of le was also replaced by an acetate to give 1j which was hydrolyzed to give the hydroxy acid Ik. The amino acid ii and the hydroxy acid Ik both were cyclized to the bridged cyclosporin lactam 2a and lactone 2b, respectively. Degradation of the MeBmt residue of the acid 1l with ozone followed by reduction gave the hydroxy acid 3 which was cyclized to a mixture of the bridged lactone 4 and the dimeric bislactone 5.

  DOI：

  10.1021/jo00120a034
• 作为产物：
  描述：

  O-Acetyl--D-serine>⁸-cyclosporin 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 sodium iodide 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ¹--D-serine>⁸-cyclosporin
  参考文献：
  名称：

  Bridged Cyclosporins

  摘要：

  The primary hydroxyl group of [D-serine](8)-cyclosporin (1b) was alkylated with isopropyl bromoacetate to provide the O-alkylated compound Ic. Then the secondary hydroxyl group was acetylated to give Id. The allylic methyl group of the MeBmt was brominated giving le. Bromide le was converted to the azide If. Transesterification of the isopropyl ester If to the methyl ester Ig and subsequent hydrolysis provided acid Ih. Reduction of the azide gave the amino acid ii. The bromide of le was also replaced by an acetate to give 1j which was hydrolyzed to give the hydroxy acid Ik. The amino acid ii and the hydroxy acid Ik both were cyclized to the bridged cyclosporin lactam 2a and lactone 2b, respectively. Degradation of the MeBmt residue of the acid 1l with ozone followed by reduction gave the hydroxy acid 3 which was cyclized to a mixture of the bridged lactone 4 and the dimeric bislactone 5.

  DOI：

  10.1021/jo00120a034