Synthesis of 2,3,4,6-tetra- O-benzyl- d-glucal on the gram scale. A convenient method for its facile synthesis and subsequent stereoselective cyclopropanation

Synthesis of 2,3,4,6-tetra- O-benzyl- d-glucal on the gram scale. A convenient method for its facile synthesis and subsequent stereoselective cyclopropanation

A new, facile synthesis of 2,3,4,6-tetra- O-benzyl- d-glucal and its subsequent cyclopropanation has been accomplished by bromination and then base-induced elimination of pent-4-enyl 2,3,4,6-tetra- O-benzyl- d-glucopyranoside. Yields and selectivities are excellent in addition to the ease of formati...

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Veröffentlicht in:Carbohydrate research 2004-03, Vol.339 (4), p.897-899
Hauptverfasser: Storkey, Corin M., Win, Anna L., Hoberg, John O.
Format: Artikel
Sprache:eng
Schlagworte:
Cyclopropanation
Cyclopropanes - chemistry
d-Glucal
Deoxyglucose - analogs & derivatives
Deoxyglucose - chemical synthesis
Deoxyglucose - chemistry
Elimination
Molecular Structure
Stereoisomerism
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Zusammenfassung:A new, facile synthesis of 2,3,4,6-tetra- O-benzyl- d-glucal and its subsequent cyclopropanation has been accomplished by bromination and then base-induced elimination of pent-4-enyl 2,3,4,6-tetra- O-benzyl- d-glucopyranoside. Yields and selectivities are excellent in addition to the ease of formation of the glycal.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2003.12.016