The isosteric phosphono analogue of α-L-rhamnose 1-phosphate has been stereoselectively synthesized by reaction of 2,3,5-tri-O-benzyl-L-rhamnose with tetraethyl methylenediphosphonate and sodium hydride in diglyme, followed by deprotection with iodotrimethylsilane. To synthesize stereoselectively the isosteric phosphono analogue of β-L-fucose 1-phosphate, 2,3,5-tri-O-benzyl-L-fuconolactone was treated with lithiated dimethyl methylenephosphonate, and the 3,4,5-tri-O-benzyl-1,7-dideoxy-1-(phosphonodimethyl)-L-galactoheptulopyranose obtained was stereoselectively reduced with triethylsilane and boron trifluoride etherate to afford the dimethyl (2,3,4-tri-O-benzyl-β-L-fucopyranosyl)methanephosphonate which was finally deprotected with iodotrimethylsilane.

Cipolla, L., LA FERLA, B., Nicotra, F., & Panza, L. (1998). Direct synthesis of the isosteric phosphono analogues of alfa-L-rhamnose 1-phosphate and alfa-L-fucose 1-phosphate. JOURNAL OF CARBOHYDRATE CHEMISTRY, 17, 1003-1013.

Direct synthesis of the isosteric phosphono analogues of alfa-L-rhamnose 1-phosphate and alfa-L-fucose 1-phosphate

CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;NICOTRA, FRANCESCO;
1998

Abstract

The isosteric phosphono analogue of α-L-rhamnose 1-phosphate has been stereoselectively synthesized by reaction of 2,3,5-tri-O-benzyl-L-rhamnose with tetraethyl methylenediphosphonate and sodium hydride in diglyme, followed by deprotection with iodotrimethylsilane. To synthesize stereoselectively the isosteric phosphono analogue of β-L-fucose 1-phosphate, 2,3,5-tri-O-benzyl-L-fuconolactone was treated with lithiated dimethyl methylenephosphonate, and the 3,4,5-tri-O-benzyl-1,7-dideoxy-1-(phosphonodimethyl)-L-galactoheptulopyranose obtained was stereoselectively reduced with triethylsilane and boron trifluoride etherate to afford the dimethyl (2,3,4-tri-O-benzyl-β-L-fucopyranosyl)methanephosphonate which was finally deprotected with iodotrimethylsilane.
Articolo in rivista - Articolo scientifico
GLYCOMIMETICS, PHOSPHONATES
English
1003
1013
11
Cipolla, L., LA FERLA, B., Nicotra, F., & Panza, L. (1998). Direct synthesis of the isosteric phosphono analogues of alfa-L-rhamnose 1-phosphate and alfa-L-fucose 1-phosphate. JOURNAL OF CARBOHYDRATE CHEMISTRY, 17, 1003-1013.
Cipolla, L; LA FERLA, B; Nicotra, F; Panza, L
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/16975
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