Glycosylation Reactions Using Phenyl(trifluoroethyl)iodonium Salts
First Claim
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1. A method of preparing a compound represented by formula I:
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Sugar-O—
R′
Icomprising the step of combining R′
—
OH, a glycosyl donor of formula II, a reagent of formula III, and a base;
whereinsaid base is selected from the group consisting of pyridine, pyrimidine, 2,6-lutidine, 2,6-di-tert-butylpyridine, 2,4,6-trimethylpyridine (collidine), diisopropylethylamine (DIPEA), 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-Bis(dimethylamino)naphthalene (Proton Sponge), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 2,4,6-tri-tert-butylpyrimidine (TTBP);
Sugar is an optionally protected monosaccharide or oligosaccharide;
O is an oxygen atom attached to an anomeric carbon atom of Sugar;
R′
is selected from the group consisting of alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and heterocyclyl;
or R′
—
OH is a steroid or an optionally protected monosaccharide, disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, or hexasaccharide, wherein O is not bonded to an anomeric carbon atom of R;
formula II is represented by;
Sugar-S—
R1
IIwhereinS is a sulfur atom attached to the anomeric carbon atom of Sugar;
R1 is a phenyl, naphthyl, ethyl, or adamantyl group, each optionally substituted with one or more substituents independently selected from the group consisting of halo, alkyl, haloalkyl, perhaloalkyl, alkoxy, and cyano;
formula III is represented by;
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Abstract
Provided are methods for the preparation of glycosylation products, including those represented by formula I:
Sugar-O—R′ I
- comprising the step of combining R′—OH, a glycosyl sulfide glycosyl donor (“thioglycoside donor”), a hypervalent iodine alkyl-transfer activating reagent, and a base. In an embodiment, the hypervalent iodine alkyl-transfer activating reagent is (phenyl(trifluoroethyl)iodonium triflimide).
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Citations
23 Claims
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1. A method of preparing a compound represented by formula I:
-
Sugar-O—
R′
Icomprising the step of combining R′
—
OH, a glycosyl donor of formula II, a reagent of formula III, and a base;wherein said base is selected from the group consisting of pyridine, pyrimidine, 2,6-lutidine, 2,6-di-tert-butylpyridine, 2,4,6-trimethylpyridine (collidine), diisopropylethylamine (DIPEA), 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-Bis(dimethylamino)naphthalene (Proton Sponge), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 2,4,6-tri-tert-butylpyrimidine (TTBP); Sugar is an optionally protected monosaccharide or oligosaccharide; O is an oxygen atom attached to an anomeric carbon atom of Sugar; R′
is selected from the group consisting of alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and heterocyclyl;
or R′
—
OH is a steroid or an optionally protected monosaccharide, disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, or hexasaccharide, wherein O is not bonded to an anomeric carbon atom of R;formula II is represented by;
Sugar-S—
R1
IIwherein S is a sulfur atom attached to the anomeric carbon atom of Sugar; R1 is a phenyl, naphthyl, ethyl, or adamantyl group, each optionally substituted with one or more substituents independently selected from the group consisting of halo, alkyl, haloalkyl, perhaloalkyl, alkoxy, and cyano; formula III is represented by; - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23)
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Specification