Solid-phase synthesis of 1,3-oxazolidine derivatives

Heong Sub Oh; Hoh Gyu Hahn; Seung Hoon Cheon; Deok Chan Ha

doi:10.1016/S0040-4039(00)00775-9

Solid-phase synthesis of 1,3-oxazolidine derivatives

Heong Sub Oh, Hoh Gyu Hahn, Seung Hoon Cheon, Deok Chan Ha

College of Science

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

1,3-Oxazolidines 9 were synthesized by using a solid support. Regioselective ring opening of resin-bound epoxy ether 3 with ammonium chloride followed by nucleophilic substitution with sodium azide gave azido alcohol 7. Reduction of 7 provided 1-amino-2-alkanol 6, which was treated with various aldehydes and acyl chlorides or isocyanates to afford the corresponding 1,3-oxazolidines immobilized on Wang resin. Oxidative cleavage with DDQ from the solid support yielded 1,3-oxazolidines as a mixture of 10 (cis) and 11 (trans). (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	5069-5072
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(00)00775-9
Publication status	Published - 2000 Jun 24

Keywords

1,3-oxazolidine
Diabetes
Oxidative cleavage
Solid phase synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Solid-phase synthesis of 1,3-oxazolidine derivatives",

abstract = "1,3-Oxazolidines 9 were synthesized by using a solid support. Regioselective ring opening of resin-bound epoxy ether 3 with ammonium chloride followed by nucleophilic substitution with sodium azide gave azido alcohol 7. Reduction of 7 provided 1-amino-2-alkanol 6, which was treated with various aldehydes and acyl chlorides or isocyanates to afford the corresponding 1,3-oxazolidines immobilized on Wang resin. Oxidative cleavage with DDQ from the solid support yielded 1,3-oxazolidines as a mixture of 10 (cis) and 11 (trans). (C) 2000 Elsevier Science Ltd.",

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year = "2000",

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T1 - Solid-phase synthesis of 1,3-oxazolidine derivatives

AU - Oh, Heong Sub

AU - Hahn, Hoh Gyu

AU - Cheon, Seung Hoon

AU - Ha, Deok Chan

PY - 2000/6/24

Y1 - 2000/6/24

N2 - 1,3-Oxazolidines 9 were synthesized by using a solid support. Regioselective ring opening of resin-bound epoxy ether 3 with ammonium chloride followed by nucleophilic substitution with sodium azide gave azido alcohol 7. Reduction of 7 provided 1-amino-2-alkanol 6, which was treated with various aldehydes and acyl chlorides or isocyanates to afford the corresponding 1,3-oxazolidines immobilized on Wang resin. Oxidative cleavage with DDQ from the solid support yielded 1,3-oxazolidines as a mixture of 10 (cis) and 11 (trans). (C) 2000 Elsevier Science Ltd.

AB - 1,3-Oxazolidines 9 were synthesized by using a solid support. Regioselective ring opening of resin-bound epoxy ether 3 with ammonium chloride followed by nucleophilic substitution with sodium azide gave azido alcohol 7. Reduction of 7 provided 1-amino-2-alkanol 6, which was treated with various aldehydes and acyl chlorides or isocyanates to afford the corresponding 1,3-oxazolidines immobilized on Wang resin. Oxidative cleavage with DDQ from the solid support yielded 1,3-oxazolidines as a mixture of 10 (cis) and 11 (trans). (C) 2000 Elsevier Science Ltd.

KW - 1,3-oxazolidine

KW - Diabetes

KW - Oxidative cleavage

KW - Solid phase synthesis

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