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

Article abstract of DOI:10.1080/07328309808001879

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.

Full text of DOI:10.1080/07328309808001879

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Journal of Carbohydrate Chemistry
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Direct Synthesis of the Isosteric
Phosphono Analogues of α-L-Rhamnose
1-Phosphate and β-L-Fucose 1-Phosphate
Laura Cipolla a , Barbara La Ferla a , Luigi Panza a & Francesco
Nicotra a
a Dipartimento di Chimica Organica e Industriale , Università degli
Studi di Milano, CNR Centro di Studio sulle Sostanze Organiche
Naturali , Via Venezian 21, 20133, Milano
Published online: 22 Aug 2006.
To cite this article: Laura Cipolla , Barbara La Ferla , Luigi Panza & Francesco Nicotra (1998) Direct
Synthesis of the Isosteric Phosphono Analogues of α-L-Rhamnose 1-Phosphate and β-L-Fucose 1-
Phosphate, Journal of Carbohydrate Chemistry, 17:7, 1003-1013, DOI: 10.1080/07328309808001879
To link to this article: http://dx.doi.org/10.1080/07328309808001879
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