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Lactosamine from lactulose via the Heyns rearrangement: a practical protocol
Univ Bangor, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales..
Univ Bangor, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales..
Univ Bangor, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales..ORCID-id: 0000-0002-8513-1952
2013 (Engelska)Ingår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 54, nr 30, s. 3960-3961Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

The Heyns rearrangement is possibly one of the oldest, easiest and most economic ways to synthesise 2-deoxy-2-amino sugars. Initially reported yields were disappointingly low, but in the late 90s Wrodnigg and Stutz discovered modified reaction conditions that gave substantially increased yields, making the reaction viable on preparative scale. Requiring larger amounts of N-acetyl lactosamine, we utilised the reported reaction conditions and found that additional modifications, especially in the work-up procedure-for example employing rapid filtration of crude diethyl ether precipitates, were necessary to make this approach robust in the research laboratory environment.

Ort, förlag, år, upplaga, sidor
PERGAMON-ELSEVIER SCIENCE LTD , 2013. Vol. 54, nr 30, s. 3960-3961
Nyckelord [en]
Heyns rearrangement, N-Acetyllactosamine lactulose, 2-Deoxy-2-amino sugar
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Organisk kemi
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URN: urn:nbn:se:kth:diva-305699DOI: 10.1016/j.tetlet.2013.05.086ISI: 000321413000013Scopus ID: 2-s2.0-84879411853OAI: oai:DiVA.org:kth-305699DiVA, id: diva2:1617202
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QC 20211206

Tillgänglig från: 2021-12-06 Skapad: 2021-12-06 Senast uppdaterad: 2022-06-25Bibliografiskt granskad

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Lahmann, Martina

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