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Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose

✍ Scribed by Rosa M. de Lederkremer; Carla Marino; Oscar Varela

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 617 KB
Volume: 200
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)84193-x

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✦ Synopsis

Benzoylation of o-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23", gave the 2,6-dibenzoate (2,62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-0-benzoyl-a#o-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-0-(2,3,5,6-tetra-O-~nzoyl-~-o-galactofuranosyl)-~galactono-1,4-lactone (4,70%), HO-3 ofwhich was benzoylated to give 5. The structure of4 was confirmed by its conversion into crystalline /I-D-Galj(1 +5)-o-Gal-ol(8). Reduction of the lactone function of 5 with di-isoamylborane followed by debcnzoylation gave P-o-&f-(1-+5)-DGalf(7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-0-(2,3,5,6-tetra-O-~n~yl-~-~galactofuranosyl)-o-galactono-I $-k&one (9), which wasconverted, as for 5, into/?-o-Galf-(I +3)[B-o-Gal&( 1-5) I-D-Galf(l3).

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