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Volumn , Issue 12, 2008, Pages 1907-1909

Novel N,S-phenacyl protecting group and its application for peptide synthesis

Author keywords

Alkyl halides; Magnesium; Peptides; Protecting groups; Thiols

Indexed keywords

ACETIC ACID; AROMATIC COMPOUND; MAGNESIUM; PHENACYL GROUP; THIOL GROUP;

ALKYLATION; ARTICLE; DEPROTECTION REACTION; PEPTIDE SYNTHESIS;

EID: 48349136603 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077887 Document Type: Article

Times cited : (16)

References (16)

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16
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- Synthesis of Substrate Materials 1-12; Typical Protection Procedure To an ice-cooled solution of amino or thio compound (5 mmol) in EtOAc (20 mL) was added Et3N (0.55 g, 5.5 mmol) and phenacyl bromide (1.1 g, 5.5mmol, After stirring at r.t. for 4 h, the reaction mixture was diluted with EtOAc (25 mL, The organic layer was washed with brine (10 mL, sat. NaHCO3 (10 mL, brine (2 x 10 mL, dried over Na 2SO4, and filtered. The filtrate was evaporated in vacuo and the crude product was purified by silica gel chromatography using a mixture of PE-EtOAc. Typical Deprotection Procedure To a solution of the protected substrate (2 mmol) in MeOH (15 mL) was added AcOH (1.5 mL, 24 mmol) and Mg turnings (288 mg, 12 mmol, The solution was stirred for 50-70 min (followed by TLC) at r.t. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was diluted with 5% NaHCO3 (10 mL, EtOAc 2 x 10 mL
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