The asymmetric synthesis of the 2-O-benzyl-3,4-dideoxy-3-fluoro-[α]-D- -hexopyranose (11), the -L--, the -D--, and the -L-- analogues (12 - 14) has been realized through dihydroxylation of the double bond of (5S)-5-benzyloxy-4-fluoro-6-[(R)-(4-methylphenyl)sulphinyl]-hex-1-ene (4) followed by oxidative removal of the chiral auxiliary sulphinyl group. A detailed spectroscopic analysis of the four fluorocarbohydrates 11 - 14 has also been performed.
Synthesis of four homochiral 3,4-dideoxy-3-fluoro-hexoses from a non-carbohydrate precursor
BRAVO, PIERFRANCESCO;RESNATI, GIUSEPPE
1990-01-01
Abstract
The asymmetric synthesis of the 2-O-benzyl-3,4-dideoxy-3-fluoro-[α]-D- -hexopyranose (11), the -L--, the -D--, and the -L-- analogues (12 - 14) has been realized through dihydroxylation of the double bond of (5S)-5-benzyloxy-4-fluoro-6-[(R)-(4-methylphenyl)sulphinyl]-hex-1-ene (4) followed by oxidative removal of the chiral auxiliary sulphinyl group. A detailed spectroscopic analysis of the four fluorocarbohydrates 11 - 14 has also been performed.File in questo prodotto:
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