27851-16-7Relevant articles and documents
Synthesis of methyl O-α-L-rhamnopyranosyl-(12)-α-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue
Mulard, Laurence A.,Kovac, Pavol,Glaudemans, Cornelis P. J.
, p. 213 - 232 (2007/10/02)
The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl α-D-galactopyranoside.Deoxygenation was achieved via activation of a protected methyl α
Stereocontrolled lincomycin synthesis
Knapp,Kukkola
, p. 1632 - 1636 (2007/10/02)
The synthesis from methyl α-D-galactopyranoside (6) of methyl thiolincosaminide (2), the direct synthetic precursor to lincomycin (1), is presented. The key step for controlling the off-pyranose stereocenters C-6 and C-7 is a novel intramolecular nitrogen delivery reaction using epoxy alcohol 10. Reaction of 10 with dimethylcyanamide in the presence of sodium hydride and imidazole leads to the oxazoline 14, a protected vicinal amino alcohol. The synthesis is completed by efficient exchange of acetal for thioacetal, followed by hydrolysis of the oxazoline and removal of the benzyl groups. The target 2 is obtained in 22 steps and 28% overall yield from 6.
Selective benzylation of some D-galactopyranosides
Flowers, Harold M.
, p. 418 - 423 (2007/10/02)
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