Ring closure via microwave-assisted intramolecular OMs displacement by a γ-OBn group (O-nucleophilic attack) in protected polyhydroxylated N-Boc-thiazolylalkyl amines afforded C-furanosides (37-81%) featuring a chiral thiazolylmethylamino side chain, which, upon thiazole to carboxylate (through aldehyde) transformation, furnished enantiopure C-furanosyl glycines. © Georg Thieme Verlag Stuttgart.
A Serendipitous Discovery of a New C-Furanosyl Glycine Synthesis via Thiazole-Based Aminohomologation of Hexopyranoses
DONDONI, Alessandro;MASSI, Alessandro;NUZZI, Andrea
2007
Abstract
Ring closure via microwave-assisted intramolecular OMs displacement by a γ-OBn group (O-nucleophilic attack) in protected polyhydroxylated N-Boc-thiazolylalkyl amines afforded C-furanosides (37-81%) featuring a chiral thiazolylmethylamino side chain, which, upon thiazole to carboxylate (through aldehyde) transformation, furnished enantiopure C-furanosyl glycines. © Georg Thieme Verlag Stuttgart.File in questo prodotto:
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