Abstract
[reaction: see text] A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Ethers, Cyclic / chemical synthesis
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Fructose / analogs & derivatives
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Fructose / chemistry*
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Glycoside Hydrolases / antagonists & inhibitors
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Imino Pyranoses / chemical synthesis
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Imino Pyranoses / chemistry
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Imino Pyranoses / pharmacology
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Mannitol / analogs & derivatives*
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Mannitol / chemical synthesis
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Mannitol / chemistry
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Mannitol / pharmacology
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Models, Molecular
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Molecular Structure
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Sorbitol / analogs & derivatives*
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Sorbitol / chemical synthesis
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Sorbitol / chemistry
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Sorbitol / pharmacology
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Stereoisomerism
Substances
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2,5-dideoxy-2,5-imino-D-glucitol
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2,5-dideoxy-2,5-imino-D-mannitol
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Ethers, Cyclic
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Imino Pyranoses
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Fructose
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Mannitol
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Sorbitol
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Glycoside Hydrolases