1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12. [GRAPHICS]
LA FERLA, B., Bugada, P., Nicotra, F. (2006). Synthesis of the dimethyl ester of 1-deoxy-L-idonojirimycin-1-methylenphosphonate: A new approach to iminosugar phosphonates. JOURNAL OF CARBOHYDRATE CHEMISTRY, 25(2-3), 151-162 [10.1080/07328300600731990].
Synthesis of the dimethyl ester of 1-deoxy-L-idonojirimycin-1-methylenphosphonate: A new approach to iminosugar phosphonates
LA FERLA, BARBARA;NICOTRA, FRANCESCO
2006
Abstract
1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12. [GRAPHICS]
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