کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1389447 | 982882 | 2006 | 5 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
![عکس صفحه اول مقاله: Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides](/preview/png/1389447.png)
چکیده انگلیسی
Genistein and orobol 8-C-β-d-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of 1 and 3 and synthesized by a C-glycosylation method involving the O→C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using Tl(NO3)3, followed by acid-catalyzed cyclization; (3) a final debenzylation by hydrogenolysis.
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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 341, Issue 9, 3 July 2006, Pages 1091–1095
Journal: Carbohydrate Research - Volume 341, Issue 9, 3 July 2006, Pages 1091–1095
نویسندگان
Shingo Sato, Kaoru Hiroe, Toshihiro Kumazawa, Onodera Jun-ichi,