کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1389423 982879 2009 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Efficient and practical synthesis of l-hamamelose
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Efficient and practical synthesis of l-hamamelose
چکیده انگلیسی

An efficient synthetic route of l-hamamelose was successfully accomplished starting from d-ribose. l-Hamamelose was synthesized in 42% overall yield with six reaction steps via a stereoselective Grignard reaction, a stereoselective crossed aldol reaction and a controlled oxidative cleavage of the double bond of a vinyl diol compound. During the oxidative cleavage of the double bond of the vinyl diol compound with osmium tetroxide and NaIO4, an over-oxidative cleavage of α-hydroxyl aldehyde generated from ring opening of the first cleaved product, formyl lactol, did not occur, probably due to the stability of the lactol form. A plausible mechanism for the stereoselective crossed aldol reaction was suggested. The final target compound, l-hamamelose can play a very important role as a chiral building block in synthesizing a wide variety of enantiopure compounds.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 344, Issue 17, 23 November 2009, Pages 2317–2321
نویسندگان
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