Abstract
A new synthetic route of N-acetyllactosamine is described. This starts from 2-O-tosylate or 2, 3'-di-O-tosylate of 1, 6-anhydro-4', 6'-O-benzylidene-β-lactose (1), which is the primary or the secondary major product of partial tosylation of compound 1 as reported in Part VIII of this series (T. Takamura and S. Tejima, Chem. Pharm. Bull. (Tokyo), 26, 1117 (1978)). The final product is isolated in about 10% yield from compound 1 via the following series of reaction : 1), monoepoxide formation, 2), azidolysis of the epoxide, 3), acetolysis of the azido sugar, 4), reduction of the azido group to amino group, followed by acetylation, and 5), de-O-acetylation.
