کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1347256 980302 2009 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enantiopure β3-neopentylglycine: synthesis and resolution
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Enantiopure β3-neopentylglycine: synthesis and resolution
چکیده انگلیسی

A procedure has been developed for the large scale synthesis of enantiopure β3-neopentylglycine and its Cbz-protected derivative. The synthetic route developed in our laboratory features Cbz-protection of the racemic β-amino acid followed by resolution with l-norephedrine and provides the enantiomerically pure Cbz-β-neopentylglycine in good yield and excellent enantiopurity. No toxic or dangerous chemicals are used, allowing the scale-up of this procedure without major safety concerns.

Figure optionsDownload as PowerPoint slide

(S)-3-Benzyloxycarbonylamino-4,4-dimethylpentanoic acid, l-(−)-Norephedrine saltC24H34N2O5[α]D20=-6.4 (c 1, EtOH)Source of chirality: resolutionAbsolute configuration: (S)

(S)-3-Benzyloxycarbonylamino-4,4-dimethylpentanoic acid; (S)-Cbz-β-neo-pentylglycineC15H21NO4[α]D20=+13.4 (c 1.4, CHCl3)Source of chirality: resolutionAbsolute configuration: (S)

(S)-3-Amino-4,4-dimethylpentanoic acid; (S)-β-neopentylglycineC7H15NO2[α]D20=-67.7 (c 1, H2O)Source of chirality: resolutionAbsolute configuration: (S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 4, 11 March 2009, Pages 478–482
نویسندگان
, , , , , , , , , , , ,