Method of preparing peracetyl oxazolines
AssigneeThe General Hospital Corporation
InventorsChristopher Warren, Satoru Nakabayashi, Roger W. Jeanloz
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Abstract
This invention relates to a method of producing peracetyl oxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reactive compound, such as trifilic acid, to directly produce the peracetyl oxazoline.
Claims7
A process for the production of a peracetyl oxazoline comprising reacting a peracetyl saccharide with a reactive compound selected from the group consisting of trifluoromethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate, silver trifluoromethanesulfonate, sodium trifluoromethanesulfonate, trifluoromethanesulfonic anhydride, and trifluoromethanesulfonyl chloride,
- wherein said reactive compound is capable of generating the formation of an intermediate saccharide acetoxonium, ion to produce a peracetyl oxazoline.
A process for the synthesis of a peracetyl glycosyl phosphate comprising the steps of:
- (a) reacting a peracetyl saccharide with a reactive compound selected from the group consisting of trifluoromethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate, silver trifluoromethanesulfonate, sodium trifluoromethanesulfonate, trifluoromethanesulfonic anhydride, and trifluoromethanesulfonyl chloride,
- wherein said reactive compound is capable of generating the formation of an intermediate saccharide acetoxonium ion, to produce a peracetyl oxazoline, and
- (b) phosphorylating said peracetyl oxazoline to produce a peracetyl glycosyl phosphate.
A process for the synthesis of a glycopeptide comprising the steps of:
- (a) reacting a peracetyl saccharide with a reactive compound selected from the group consisting of trifluoromethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate, silver trifluoromethanesulfonate, sodium trifluoromethanesulfonate, trifluoromethanesulfonic anhydride, and trifluoromethanesulfonyl chloride,
- wherein said reactive compound is capable of generating the formation of an intermediate saccharide acetoxonium ion to produce a peracetyl oxazoline;
- (b) reacting said peracetyl oxazoline with an azide to produce a glycosyl azide;
- (c) hydrogenating said glycosyl azide to produce a glycosyl amine;
- and
- (d) coupling said glycosyl amine with an exposed carboxylic group in an amino acid or peptide.
A process for the synthesis of oligoglycosides comprising the steps of:
- (a) reacting a peracetyl saccharide with a reactive compound selected from the group consisting of trifluoromethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate, silver trifluoromethanesulfonate, sodium trifluoromethanesulfonate, trifluoromethanesulfonic anhydride, and trifluoromethanesulfonyl chloride,
- wherein said reactive compound is capable of generating the formation of an intermediate saccharide acetoxonium ion to produce a peracetyl oxazoline, and,
- (b) reacting said peracetyl oxazoline with a thiol compound in the presence of boron trifluoride.
Dependencies are inferred from the claim text.