Total stereoselective syntheses of β-C-manno-pyranosides and of β- C(1←3)-linked disaccharides

Article abstract of DOI:10.1016/S0040-4039(99)00432-3

(-)-7-Oxabicyclo[2.2.1]hept-5-en-2-one has been convened to (-)-6-exo- [(tert-butyl)dimethylsilyloxy]-7-endo-benzyloxy-8-oxabieyclo[3.2.1]oct-3-en- 2-one and methyl 3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-D-glycero-D-galacto- heptouronate that were condensed with Me₂AlSPh into a single aldol which was transformed into a β-D-ManAp-CH(OAe)(1←3)-α-L-GulAp-CH(SEt)₂ derivative.