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US 4,228,080 AGranted
Process for the preparation of methyl 3,4-anhydro-2,6-dideoxy-L-ribo-hexopyranoside
AssigneeHoffmann-La Roche Inc.
InventorsGuenter Grethe, Milan R. Uskokovic, John Sereno
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Abstract
A process to produce methyl 3,4-anhydro-2,6-dideoxy-L-ribohexopyranoside, its enantiomer and racemate thereof. The compound is useful as an intermediate in the production of daunosamine which in turn is a prime constituent in the anti-cancer agents Daunomycin and Adriamycin. Also disclosed are novel intermediates in the process.
Claims1
A process to produce a compound of the formula ##STR2## its enantiomer and racemate thereof which comprises (a) oxidizing a compound of the formula ##STR3## its enantiomer and racemate thereof with an aromatic or aliphatic peracid in an inert organic solvent,
- (b) oxidizing the product of (a) with an oxidizing agent selected from the group consisting of sodium or potassium dichromate, chromium trioxide or an aliphatic or aromatic peracid,
- (c) oxidizing the product of (b) with an aromatic or aliphatic peracid in an inert organic solvent,
- (d) reducing the product of (c) with a reducing agent selected from the group consisting of diisobutylaluminum hydride, diborane, sodium or lithium triethoxyaluminumhydride, sodium-bis (2-methoxyethoxy)aluminumhydride and tri-t-butoxyalumino-hydride and
- (e) reacting the product of (d) with methanol in the presence of an acid catalyst.
1 more element
Dependencies are inferred from the claim text.