Thio linked glycosyl compounds
OwnerChi-Huey Wong, Hirosato Kondoinventors
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Abstract
Thio linked glycosyl compounds are disclosed and synthesized. The synthesis employs a blocked carbohydrate donor and a blocked glycosyl acceptor. The carbohydrate donor includes an acid labile phosphite leaving group attached to the anomeric carbon. The blocked glycosyl acceptor includes an unprotected thio group susceptible to electrophilic attack. The reaction is initiated by the addition of a Lewis acid so as to activate the acid labile phosphite leaving group on the carbohydrate donor. The substitution reaction may be conducted at -78.degree. C. in a solvent such as Et.sub.3 N which favors the formation of thio linked glycosylation products.
Claims8
A substitution reaction for producing thio linked glycosylation products comprising the following steps:
- Step A:
- providing a blocked carbohydrate donor having an anomeric carbon with an acid labile phosphite leaving group attached thereto;
- Step B:
- providing a blocked glycosyl acceptor having an unprotected thio group susceptible to electrophilic substitution, the blocked glycosyl acceptor being p-methoxythiophenol;
- Step C:
- providing a promotor having Lewis acid activity for catalyzing the phosphite leaving group of said Step A;
- then
- Step D:
- reacting the blocked carbohydrate donor of said Step A with the blocked glycosyl acceptor of said Step B in the presence of the promotor of said Step C within a solvent favoring the formation of thio linked glycosylation products;
- and then
- Step E:
- quenching the reaction of said Step D.
A substitution reaction for producing thio linked glycosylation products comprising the following steps:
- Step A:
- providing a blocked carbohydrate donor having an anomeric carbon with an acid labile phosphite leaving group attached thereto;
- Step B:
- providing a blocked glycosyl acceptor having an unprotected thio group susceptible to electrophilic substitution;
- Step C:
- providing a promotor having Lewis acid activity for catalyzing the phosphite leaving group of said Step A, the promotor being trimethylsilyl trifluoromethanesulfonate (TMSOTf);
- then
- Step D:
- reacting the blocked carbohydrate donor of said Step with the blocked glycosyl acceptor of said Step B in the presence of the promotor of said Step C within a solvent favoring the formation of thio linked glycosylation products;
- and then
- Step E:
- quenching the reaction of said Step D.
A substitution reaction for producing thio linked glycosylation products comprising the following steps:
- Step A:
- providing a blocked carbohydrate donor having an anomeric carbon with an acid labile phosphite leaving group attached thereto;
- Step B:
- providing a blocked glycosyl acceptor having an unprotected thio group susceptible to electrophilic substitution;
- Step C:
- providing a promotor having Lewis acid activity for catalyzing the phosphite leaving group of said Step A;
- then
- Step D:
- reacting the blocked carbohydrate donor of said Step A with the blocked glycosyl acceptor of said Step B in the presence of the promotor of said Step C within a solvent favoring the formation of thio linked glycosylation products;
- and then
- Step E:
- quenching the reaction of said Step D by the addition of Et.sub.3 N and followed by washing the glycosylation products with saturated NaHCO.sub.3.
A substitution reaction for producing thio linked glycosylation products comprising the following steps:
- Step A:
- providing a blocked carbohydrate donor having an anomeric carbon with an acid labile phosphite leaving group attached thereto, the phosphite leaving group being dibenzyl phosphite;
- Step B:
- providing a blocked glycosyl acceptor having an protected thio group susceptible to electrophilic substitution;
- Step C:
- providing a promotor having Lewis acid activity for catalyzing the phosphite leaving group of said Step A;
- then
- Step D:
- reacting the blocked carbohydrate donor of said Step A with the blocked glycosyl acceptor of said Step B in the presence of the promotor of said Step C within a solvent favoring the formation of thio linked glycosylation products;
- and then
- Step E:
- quenching the reaction of said Step D.
p-Methoxyphenyl 6-deoxy-1-thio-.beta.-L-galactopyranose.
p-Methoxyphenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-.beta.-L-galactopyranose.
Dependencies are inferred from the claim text.