Pivalates in the selective protection and activation of maltose for the synthesis of sulfated 3-deoxy-maltosyl-(1 → 4)-α,α-trehalose
| Autor: | Hans Peter Wessel, Michel Trumtel |
|---|---|
| Rok vydání: | 1997 |
| Předmět: |
Magnetic Resonance Spectroscopy
Glycosylation Molecular Structure Trimethylsilyl Sulfates Stereochemistry Molecular Sequence Data Organic Chemistry Oligosaccharides Trehalose General Medicine Maltose Biochemistry Analytical Chemistry chemistry.chemical_compound Sulfation Carbohydrate Sequence Pyranose chemistry Yield (chemistry) Tetrasaccharide Derivative (chemistry) |
| Zdroj: | Carbohydrate Research. 297:163-168 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(96)00262-5 |
| Popis: | Pivaloylation of maltose gave, in satisfactory yield, 1,2,6,2′,3′,4′,6′-hepta- O -pivaloyl-β-maltose which was converted to the 3-deoxygenated analogue in a Barton-McCombie reaction. This compound was used directly in a trimethylsilyl triflate-mediated glycosylation reaction with 2,3,6-tri- O -benzyl-α- d -glucopyranosyl 2,3-di- O -benzyl-4,6- O -benzylidene-α- d -glucopyranoside to give the corresponding maltosyl-(1 → 4)-α,α-trehalose derivative. After deprotection, the monodeoxygenated tetrasaccharide was sulfated; in the reaction product, one compound fully sulfated at the outer pyranose rings predominated. © 1997 Elsevier Science Ltd. |
| Databáze: | OpenAIRE |
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