{"id":330,"date":"2017-02-02T10:20:08","date_gmt":"2017-02-02T09:20:08","guid":{"rendered":"https:\/\/sites.unimi.it\/apisgroup\/?p=330"},"modified":"2022-01-21T15:34:31","modified_gmt":"2022-01-21T14:34:31","slug":"novel-synthetic-approach-to-the-racemic-neuraminidase-inhibitor-peramivir","status":"publish","type":"post","link":"https:\/\/sites.unimi.it\/apisgroup\/2017\/02\/02\/novel-synthetic-approach-to-the-racemic-neuraminidase-inhibitor-peramivir\/","title":{"rendered":"A novel synthetic approach to the racemic Neuraminidase inhibitor Peramivir"},"content":{"rendered":"

\"grafabst1\"An advanced intermediate in the synthesis of the racemic Neuraminidase inhibitor Peramivir was synthesised
\nin a new and versatile manner starting from a stereoselective 1,3-dipolar cycloaddition reaction
\nbetween the nitrile oxide deriving from 2-ethylbutanal and the commercially available and inexpensive
\nbicyclo[2.2.1]hepta-2,5-diene. The reaction mainly afforded the exo-isoxazolino-norbornene derivative
\nfrom which the oxidative cleavage of the carbonecarbon double bond followed by subsequent dehydration
\nled to the corresponding anhydride intermediate. Amines and alcohols were used as nucleophiles for
\nopening the anhydride, with amines providing the better results. Both the monoesteremonoacid and the
\nmonoesteremonoamide were transformed into the monoesteremonoamino intermediate fromwhich the
\nsynthesis continued using previously published methods. In the best protocol, the total yield of this key
\nintermediate was increased up to 17% from bicyclo[2.2.1]hepta-2,5-diene.<\/p>\n

Tetrahedron<\/em> 72<\/strong> (2016) 7975e7981<\/p>\n","protected":false},"excerpt":{"rendered":"

An advanced intermediate in the synthesis of the racemic Neuraminidase inhibitor Peramivir was synthesised in a new and versatile manner starting from a stereoselective 1,3-dipolar cycloaddition reaction between the nitrile oxide deriving from 2-ethylbutanal...<\/p>\n","protected":false},"author":1,"featured_media":342,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6,7],"tags":[],"class_list":["post-330","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-application","category-amino-acid"],"yoast_head":"\nA novel synthetic approach to the racemic Neuraminidase inhibitor Peramivir - APIS group<\/title>\n<meta name=\"robots\" content=\"noindex, follow\" \/>\n<meta property=\"og:locale\" content=\"it_IT\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"A novel synthetic approach to the racemic Neuraminidase inhibitor Peramivir - 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