کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1389185 982849 2007 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
An improved synthesis of a key intermediate for (+)-biotin from d-mannose
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
An improved synthesis of a key intermediate for (+)-biotin from d-mannose
چکیده انگلیسی

An efficient and reproducible process for the synthesis of methyl 2,3,4,5-tetradeoxy-7,8-O-isopropylidene-d-arabino-nanonate (2), a key intermediate in the total synthesis of (+)-biotin (1), starting from readily available d-mannose is described. The crucial part of this synthesis was the development of a practical route to a novel O-benzyl protected unsaturated ester methyl (benzyl 5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-d-lyxo-nona-5,7-dienofuranosid) uronate (7), allowing the one-step preparation of hydroxy ester methyl 5,6,7,8-tetradeoxy-2,3-O-isopropylidene-α-d-lyxo-nanofuranuronate (8) by the catalytic debenzylation and hydrogenation over palladium on carbon catalyst. This procedure requires no chromatographic purification, which makes it ideal for synthetic preparation on an industrial scale.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 342, Issue 16, 26 November 2007, Pages 2461–2464
نویسندگان
, , , , ,