Iodine(III)-Promoted azide transfer to 3-deoxyglycals

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OriginalspracheEnglisch
Seiten (von - bis)767-769
Seitenumfang3
FachzeitschriftSynlett
Jahrgang1995
Ausgabenummer7
PublikationsstatusVeröffentlicht - Juli 1995
Extern publiziertJa

Abstract

Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.

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Iodine(III)-Promoted azide transfer to 3-deoxyglycals. / Kirschning, Andreas; Domann, Silvie; Dräger, Gerald et al.
in: Synlett, Jahrgang 1995, Nr. 7, 07.1995, S. 767-769.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Kirschning A, Domann S, Dräger G, Rose L. Iodine(III)-Promoted azide transfer to 3-deoxyglycals. Synlett. 1995 Jul;1995(7):767-769. doi: 10.1055/s-1995-5051
Kirschning, Andreas ; Domann, Silvie ; Dräger, Gerald et al. / Iodine(III)-Promoted azide transfer to 3-deoxyglycals. in: Synlett. 1995 ; Jahrgang 1995, Nr. 7. S. 767-769.
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AU - Kirschning, Andreas

AU - Domann, Silvie

AU - Dräger, Gerald

AU - Rose, Lars

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N2 - Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.

AB - Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.

KW - azidoglycal

KW - hypervalent iodine

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KW - Mitsunobu reaction

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