benzyloxycarbonyl-L-alanine L-threonine L-alanine benzyl ester → N-carbobenzyloxyalanine

HRID 394820

反応式

HRID 394820 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H](C(O)=O)[C@@H](C)O.C(OC(=O)[C@H](C)N)C1C=CC=CC=1>ClCCl.[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2].Cl([O-])(=O)(=O)=O.[Ag+]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 1

HCID 69975378benzyloxycarbonyl-L-alanine L-threonine L-alanine benzyl ester

生成物 1

HCID 736104N-carbobenzyloxyalanine

試薬・触媒・溶媒 3

HCID 24562Silver perchlorate触媒HCID 131724019Zirconocene chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Zirconocene chloride (Cp2ZrCl2) (543 mg, 1.86 mmol) and silver perchlorate (771 mg, 3.72 mmol) are dissolved in dichloromethane (10 ml) and thereto is added molecular sieves (1.0 g), and the reaction system is purged with nitrogen gas and stirred at room temperature for 10 minutes. To the mixture is added benzyloxycarbonyl-L-alanine-L-threonine-L-alanine benzyl ester (904 mg, 1.86 mmol) obtained in Reference Example 4, the reaction system is cooled to −40° C. The reaction mixture is added to a solution of O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1→3)-2-azido-4,6-di-O-benzyl-2-deoxy-α-D-galacto-pyranosyl fluoride (620 mg, 0.74 mmol) obtained in Reference Example 2 in dichloromethane (3 ml), and the mixture is gradually warmed to room temperature and reacted for 18 hours. The reaction is stopped by adding thereto pyridine (1 ml) and the mixture is extracted with chloroform. The organic layer is washed with an aqueous sodium hydrogen carbonate solution and a saline solution, dried over anhydrous magnesium sulfate, filtered and concentrated and separated by a silica gel column chromatography (toluene:ethyl acetate=9:1-0.5% triethylamine) to give benzyloxycarbonyl-L-alanine-(O-(2,3,4,6-tetra-O-benzyl-β-D-galacto-pyranosyl)-(1→3)-(2-azido-4,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-L-theronine-L-alanine benzyl ester (333 mg, 33%).

後処理

  1. additionis added molecular sieves (1.0 g)
  2. customthe reaction system is purged with nitrogen gas
  3. customobtained in Reference Example 4
  4. temperaturethe reaction system is cooled to −40° C
  5. temperaturethe mixture is gradually warmed to room temperature
  6. customreacted for 18 hours
  7. additionby adding
  8. extractionpyridine (1 ml) and the mixture is extracted with chloroform
  9. washThe organic layer is washed with an aqueous sodium hydrogen carbonate solution
  10. dry with materiala saline solution, dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customseparated by a silica gel column chromatography (toluene:ethyl acetate=9:1-0.5% triethylamine)

出典と根拠

ORDレコード
ord-4e33752c256e48c49ac6154c62f2bece
出典データセット
uspto-grants-2003_08
特許番号
US06602982B1

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