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Asymmetric syntheses of the methyl glycosides of 2-deoxy-2-aminohexoses: D-allosamine, D-mannosamine, D-idosamine and D-talosamine

Abstract:

A range of the methyl glycosides of 2-deoxy-2-aminohexoses, comprising d-allosamine, d-mannosamine, d-idosamine and d-talosamine, were prepared from the corresponding d-aldopentoses via a seven step synthetic sequence. The doubly diastereoselective conjugate addition of the requisite antipode of lithium N-benzyl-N-(α-methylbenzyl)amide and in situ enolate oxidation with the requisite antipode of camphorsulfonyloxaziridine (CSO) was used as the key, stereodefining step. Sequential reduction of...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2014.06.019

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON More from this journal
Volume:
70
Issue:
40
Pages:
7106-7119
Publication date:
2014-10-07
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:476788
UUID:
uuid:a6f5afeb-699b-4682-b2ca-34df4583e90f
Local pid:
pubs:476788
Source identifiers:
476788
Deposit date:
2014-11-05

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