Tetrahydropyranyl (THP) derivatives of alcohols are converted in one-pot and in stereoselective manner into the corresponding 1-O-alkyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosides on treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and trimethylsilyl triflate (TMSOTf). The same protocol was also applyed on 1-O-acetyl-2,3,4,6-tetra-O-benzyl-glucopyranoside (α/β 9:1) to give, by reaction with 1-O-methyl-2,3,4-tri-O-benzyl-6-THP-α-D-glucopyranoside, the corresponding disaccaride (α/β 3:1). The reaction is high yielding and proceeds rapidly at very mild conditions (−30°C) on easily available starting materials.
A one-pot glycosylation of tetrahydropyranyl (THP) ether intermediates
MANFREDINI, Stefano
Primo
;BARALDI, Pier GiovanniSecondo
;SIMONI, Daniele
1994
Abstract
Tetrahydropyranyl (THP) derivatives of alcohols are converted in one-pot and in stereoselective manner into the corresponding 1-O-alkyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosides on treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and trimethylsilyl triflate (TMSOTf). The same protocol was also applyed on 1-O-acetyl-2,3,4,6-tetra-O-benzyl-glucopyranoside (α/β 9:1) to give, by reaction with 1-O-methyl-2,3,4-tri-O-benzyl-6-THP-α-D-glucopyranoside, the corresponding disaccaride (α/β 3:1). The reaction is high yielding and proceeds rapidly at very mild conditions (−30°C) on easily available starting materials.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
