The synthesis of O-β-d-mannopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-D-glucopyranose. Part I
| Autor: | Christopher D. Warren, Shigeo Suzuki, Diane Power, Claudine Augé, Roger W. Jeanloz, Murray L. Laver |
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| Rok vydání: | 1980 |
| Předmět: |
chemistry.chemical_classification
Chemistry Dimethyl sulfoxide Organic Chemistry Disaccharide Sulfoxide General Medicine Biochemistry Medicinal chemistry Analytical Chemistry chemistry.chemical_compound Sodium borohydride Bromide Organic chemistry Stereoselectivity Silver trifluoromethanesulfonate Trisaccharide |
| Zdroj: | Carbohydrate Research. 82:71-83 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(00)85521-4 |
| Popis: | Allyl 2-acetamido-3,6-di-O-(2-butenyl)-2-deoxy-β- D -glucopyranoside was prepared, and coupled with 2-methyl-(4-O-acetyl-3,6-di-O-benzyl-1,2-dideoxy-α- D -glucopyrano)-[2,1-d]-2-oxazoline. The resulting, protected disaccharide allyl 2-acetamido-4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β- D -glucopyranosyl)-3,6-di-O-(2-butenyl)-2-deoxy-β- D -glucopyranoside was O-deacetylated and the product coupled with 2-O-acetyl-3,4,6-tri-O-benzyl-α- D -glucopyranosyl bromide in the presence of silver trifluoromethanesulfonate and 1, 1,3,3-tetramethylurea, to give the trisaccharide, allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-β- D -glucopyranosyl)-(1→4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β- D -glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-(2-butenyl)-2-deoxy-β- D -glucopyranoside. O-Deacetylation, oxidation with acetic anhydride-dimethyl sulfoxide, and stereoselective reduction with sodium borohydride gave mainly allyl O-(3,4,6-tri-O-benzyl-β- D -mannopyranosyl)-(1→4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β- D -glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-(2-butenyl)-2-deoxy-β- D -glucopyranoside. Removal of the 2-butenyl groups was performed by treatment with potassium tert-butoxide in dimethyl sulfoxide, followed by isomerization of the allyl to a 1-propenyl group with tris(triphenyl-phosphine)rhodium chloride. Mild, acid treatment, and catalytic hydrogenation, gave the title trisaccharide. |
| Databáze: | OpenAIRE |
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