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Asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-L-erythroside, methyl N-Boc-2-deoxy-2-amino-D-threoside and methyl N-Boc-2,3-dideoxy-3-amino-L-arabinopyranoside

Abstract:

The asymmetric syntheses of methyl N-Boc-2-deoxy-2-amino-l-erythroside and methyl N-Boc-2-deoxy-2-amino-d-threoside have been achieved from sorbic acid, in six and eight steps, and in 35 and 13% overall yield, respectively. Diastereoselective aminohydroxylation of tert-butyl sorbate gives access to two diastereoisomeric α-hydroxy-β-amino-γ,δ-unsaturated esters. Reduction of the ester functionality and ozonolysis of the double bond gives the corresponding aldehyde, which exists exclusively in ...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2014.03.055

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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:
21
Pages:
3491-3501
Publication date:
2014-05-27
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Keywords:
Pubs id:
pubs:462697
UUID:
uuid:cb3867a5-d697-4429-84ea-c4766a3bf7eb
Local pid:
pubs:462697
Source identifiers:
462697
Deposit date:
2014-06-17

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