کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5212975 | 1383140 | 2016 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Rearrangement reactions in the fluorination of d-glucopyranoside at the C-4 position by DAST
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Attempts to synthesize 4-deoxy-4-fluoro-KRN-7000 (2), a potential immune adjuvant, by fluorination of 4-hydroxy of α-d-glucopyranoside using DAST, were not successful. Instead, the unusual 5-deoxy-5-fluoro β-l-altrofurnoside and the corresponding 4-deoxy-4-fluoro α-d-glucopyranoside with retained configuration were obtained. In the presence of polar solvents, the reaction afforded the epoxide product, suggesting the bicyclic oxiranium ion intermediate to be involved in this reaction. Compound 2 was eventually achieved by treating 4-methanesufonated glucopyranoside with fluoride ion and found to be a weak agonist for CD1d and NKT cell activation.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 72, Issue 36, 8 September 2016, Pages 5571-5577
Journal: Tetrahedron - Volume 72, Issue 36, 8 September 2016, Pages 5571-5577
نویسندگان
Tzung-Sheng Lin, Wei-Tse Tsai, Pi-Hui Liang,