کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5271645 1385444 2010 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Efficient stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine via oxidation of oxime
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Efficient stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine via oxidation of oxime
چکیده انگلیسی

Stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine (20) was accomplished from (R)-Fmoc-Ser(tBu)-OH (14) in a total of six steps via an oxime. The oxime (17) was obtained from (R)-Fmoc-Ser(tBu)-H (16), which in turn was obtained by reduction of Weinreb amide (15). Oxidation of oxime was realized with peroxytrifluoroacetic acid at a neutral pH at 0 °C. After removal of the tBu protecting group with 90% TFA/H2O, the hydroxyl group was oxidized with Jones reagent to afford (S)-Fmoc-β-nitroalanine (20) in overall good yield.

Stereoselective synthesis of (S)-Fmoc-β-nitroalanine was accomplished from (R)-Fmoc-Ser(tBu)-OH in a total of six steps via oxidation of oxime.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 51, Issue 25, 23 June 2010, Pages 3340-3343
نویسندگان
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