New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group

Autor:	Toshinori Higashi, Jordi Calveras, Takeshi Sugai, Mitsuru Shoji, Israt Sultana, Yasuhito Nagai, Yuji Ueda
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Glycal Chemistry Stereochemistry Organic Chemistry Iodobenzene Regioselectivity Mannosamine Biochemistry chemistry.chemical_compound Aminosugar Drug Discovery Chemoselectivity Glucal Alkyl
Zdroj:	Tetrahedron. 66:4284-4291
ISSN:	0040-4020
Popis:	Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl- d -mannosamine (ManNAc) and the corresponding sialic acids from d -glucal were established. Lipase-catalyzed regioselective transformation of d -glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tert-butyl alcohol proceeded in manno-configured at C-2 as well as α- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f1754cf863f33eda8bbac5da06c9a2a6 https://doi.org/10.1016/j.tet.2010.04.045 Zobrazit plný text záznamu Full Text from ScienceDirect