Selective N-Debenzylation of Benzylamino Derivatives of 1,6-Anhydro-β-d-hexopyranoses

Selective N-Debenzylation of Benzylamino Derivatives of 1,6-Anhydro-β-d-hexopyranoses

When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-β-d-hexopyranoses in the d-gluco, d-lyxo, and d-arabino configurations were reacted with diisopropyl azodicarboxylate, N-benzyl groups were selectively cleaved in the presence of O-benzyl groups. The yields...

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Veröffentlicht in:Organic letters 2000-06, Vol.2 (12), p.1681-1683
Hauptverfasser: Kroutil, Jiri, Trnka, Tomas, Cerny, Miloslav
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container_title Organic letters
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creator Kroutil, Jiri
Trnka, Tomas
Cerny, Miloslav
description When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-β-d-hexopyranoses in the d-gluco, d-lyxo, and d-arabino configurations were reacted with diisopropyl azodicarboxylate, N-benzyl groups were selectively cleaved in the presence of O-benzyl groups. The yields ranged from 51 to 97%. The debenzylation of some aliphatic benzylamines is also discussed.
doi_str_mv 10.1021/ol005746g
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title Selective N-Debenzylation of Benzylamino Derivatives of 1,6-Anhydro-β-d-hexopyranoses
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