Saccharide intermediates in the formation of the calicheamicin and esperamicin oligosaccharides
AssigneeThe Scripps Research Institute
InventorsKyriacos C. Nicolaou, Robert D. Groneberg, Erwin P. Schreiner, Wilhelm Stahl
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Abstract
Intermediates useful in preparing the calicheamicin and esperamicin oligosaccharides, and particularly the sulfur- and O-substituted hydroxylamine-containing B ring of both oligosaccharides, are disclosed as are methods of making and using the same, including the preparation of chimeric antibiotics using the same.
Claims16
A compound having the structural formula ##STR34## wherein R is a moiety selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl and m-chlorophenyl;
- and
- R.sup.2 is a moiety selected from the group consisting of tri-C.sub.1 -C.sub.6 alkylsilyl, di-C.sub.1 -C.sub.6 alkylphenylsilyl, and C.sub.1 -C.sub.6 alkyldiphenylsilyl.
A compound having the structural formula ##STR35## where R.sup.1 is hydrogen or COR, and R is a moiety selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl and m- chlorophenyl;
- R.sup.2 is a moiety selected from the group consisting of tri-C.sub.1 -C.sub.6 alkylsilyl, di-C.sub.1 -C.sub.6 alkylphenylsilyl, and C.sub.1 -C.sub.6 alkyldiphenylsilyl;
- and
- --W is (i) an N-hydroxy cyclic imido group, --ON.dbd.R.sup.4, in which R.sup.4 has 4 to about 8 carbon atoms or (ii) an O,N-disubstituted oxime group, --ON.dbd.R.sup.5, that is a reaction product of a hydroxylamine and a compound that is selected from the group consisting of a C.sub.1 -C.sub.6 alkyl ketone or aldehyde and a tetrahydropyranone, with the proviso that R.sup.1 is COR when --W is --ON.dbd.R.sup.4.
A compound having the structural formula ##STR36## wherein R.sup.2 is a moiety selected from the group consisting of tri-C.sub.1 -C.sub.6 alkylsilyl, di-C.sub.1 -C.sub.6 alkylphenylsilyl, and C.sub.1 -C.sub.6 alkyldiphenylsilyl;
- --ON.dbd.R.sup.5 is an O,N-disubstituted oxime group that is a reaction product of a hydroxylamine and a compound that is selected from the group consisting of a C.sub.1 -C.sub.6 alkyl ketone or aldehyde and a tetrahydropyranone;
- and
- R.sup.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, benzoyl, m-chlorobenzoyl, C.sub.1 -C.sub.6 alkyl oxycarbonyl and N-carbonyl imidazyl.
Dependencies are inferred from the claim text.