103292-07-5Relevant articles and documents
SYNTHESIS OF 5-O-METHYL-D-GALACTOFURANOSE
Sznaidman, Marcos L.,Cirelli, Alicia Fernandez,Lederkremer, Rosa M. de
, p. 233 - 240 (2007/10/02)
5-O-Methyl-D-galactofuranose (7) was synthesized, for the first time, in five steps from D-galactono-1,4-lactone (1) in good overall yield.Tritylation and further acetylation of 1 gave 2,3,5-tri-O-acetyl-6-O-trityl-D-galactono-1,4-lactone (2); prolonged acetylation caused elimination to form 2,5-di-O-acetyl-3-deoxy-6-O-trityl-D-threo-hex-2-enono-1,4-lactone.Detritylation of 2 with BF3.Et2O occurred with acetyl migration and afforded 2,3,6-tri-O-acetyl-D-galactono-1,4-lactone (4).Methylation of 4 with CH2N2-BF3.Et2O gave 5-O-methyl-2,3,6-tri-O-acetyl-D-galactono-1,4-lactone.Subsequent reduction by disiamylborane followed by controlled deacetylation gave crystalline 7.The (1)H- and (13)C-n.m.r. spectra of 7 indicated a 1:1.3 ratio of the α and β furanose anomers.