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Reductive openings of benzylidene acetals. Kinetic studies of borane and alane activation by Lewis acids.

Författare:
Publiceringsår: 2008
Språk: Engelska
Sidor: 2997-3000
Publikation/Tidskrift/Serie: Carbohydrate research
Volym: 343
Dokumenttyp: Artikel
Förlag: Elsevier Ltd

Sammanfattning

The reaction kinetics for a number of reductive openings of methyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-d-glucopyranoside have been investigated. Openings to give free HO-6 (using BH(3).THF-AlCl(3)-THF or LiAlH(4)-AlCl(3)-Et(2)O) follow first order kinetics, while reactions yielding free HO-4 (using BH(3).NMe(3)-AlCl(3)-THF or BH(3).NMe(3)-BF(3).OEt(2)-THF) follow higher order kinetics. The addition of water to the BH(3).NMe(3)-AlCl(3)-THF results in faster reactions. The BH(3).SMe(2)-AlCl(3)-THF system constitutes a borderline case, yielding both free HO-6 (by a first order reaction) and free HO-4 (by a higher order reaction). These results correlate well with the concept of regioselectivity by activation of borane complexes.

Disputation

Nyckelord

  • Chemistry

Övrigt

Published
Yes
  • ISSN: 0008-6215

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