Process for the preparation of (1s, 2s, 6r)-4-methoxy-...

Details Process for the preparation of (1s, 2s, 6r)-4-methoxy-... Process for the preparation of (1s, 2s, 6r)-4-methoxy-...

C - Chemistry, Metallurgy

07

D

260/360.6

C07D 493/04 (2006.01) C07D 303/14 (2006.01) C07D 303/32 (2006.01)

Patent

CA 1114391

ABSTRACT OF THE DISCLOSURE A process for the preparation of (1S,2S,6R)-4- methoxy-2-methyl-3,7-dioxabicyclo[4.1.0]heptane and compounds useful as intermediates in this process. L-Daunosamine (3-amino- 2,3,6-trideoxy-L-lyxo-hexose) is the amino sugar constituent of the anthracycline antibiotics daunomycin and adriamycin (Carbohydrate Research 44 (1975) 227-240) which plays a significant role in antitumor therapy. As disclosed herein the known (1S,2S,6R)-4-methoxy-2-methyl-3,7-dioxabicyclo[4.1.0]- heptane of formula Image (VI) is used as an intermediate in the preparation of daunosamine and is prepared by methylation of 4R- and/or 4S- (1S,2S,6R)-2-methyl-3,7- dioxabicyclo[4.1.0]-heptan-4-ol of formula Image (V).

316165

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