Highly Stereoselective and Iterative Synthesis of α-(1→4)-Linked Polysaccharides Composed of 3-O-Methyl-d -mannose
| Autor: | Yoshito Kishi, Hwan-Sung Cheon, Yiqian Lian |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
chemistry.chemical_classification
Glycosylation Stereochemistry Organic Chemistry Mannose Methylmannosides Polysaccharide Biochemistry Acceptor chemistry.chemical_compound Carbohydrate Sequence chemistry Polysaccharides Carbohydrate Conformation Stereoselectivity Physical and Theoretical Chemistry Trifluoromethanesulfonate |
| Zdroj: | Organic Letters. 9:3323-3326 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol0713335 |
| Popis: | A second-generation synthesis of synthetic 3-O-methyl-D-mannose-containing polysaccharides (sMMPs) is reported. The glycosidation of donor B and acceptor C, prepared from a common precursor A in two and one steps, respectively, is effected by t-butyldimethylsilyl trifluoromethanesulfonate to furnish only the desired alpha-anomer D in high yields. Unlike the first-generation synthesis, this synthesis gives the desired product free from contamination of scrambling products. A three-step protocol is used to deprotect D to furnish sMMPs. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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