Convergent synthesis of pyrrolidine-based (1→6)- and (1→5)-aza-C-disaccharides
✍ Scribed by Alessandro Dondoni; Pier Paolo Giovannini; Alberto Marra
- Book ID
- 104210633
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 132 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A new entry to (136)-and ( 135)-aza-C-disaccharides featuring the pyrrolidine ring as the imino sugar component is described via Wittig condensation of polyhydroxylated 2-formylpyrrolidines with galactopyranose 6-phosphorane and ribofuranose 5-phosphorane, respectively.
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The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-l,2-dideoxy-D-arabino-hex-l-enitol (5a) with a variety of sugar based carboxylic acids 6a-d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d and exposure to the Schrock molybdenum catalyst