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Synthesis of (±)-branched-chain azaisonucleosides via Michael addition of 5-nitro-2,2-pentamethylene-1,3-dioxane to methyl 2-bromoacrylate

✍ Scribed by Ewa Mironiuk-Puchalska; Ewa Kołaczkowska; Wojciech Sas

Book ID: 104252220
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 165 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02012-9

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✦ Synopsis

Michael reaction of 2,2-pentamethylene-5-nitro-1,3-dioxane 1 with methyl 2-bromoacrylate, generated in situ from methyl 2,3-dibromopropanoate and triethylamine, afforded a-bromo-g-nitroester 3, which was readily converted into various 5,5-bis(hydroxymethyl)pyrrolidine analogues of nucleosides.

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