کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5212780 1383132 2016 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Divergent total synthesis of d-ribo-phytosphingosine and l-ribo-phytosphingosine from d-ribose
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Divergent total synthesis of d-ribo-phytosphingosine and l-ribo-phytosphingosine from d-ribose
چکیده انگلیسی

Divergent total synthesis of d-ribo-phytosphingosine (1) and l-ribo-phytosphingosine (2) was achieved from readily available d-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively anti-1,2-amino alcohols 12 and 17 with diastereoselectivity of 32:1 and 31:1 in 75% and 76% yields, respectively. These results could be explained by the neighboring group effect, leading to retention of stereochemistry.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 72, Issue 52, 29 December 2016, Pages 8550-8556
نویسندگان
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