Stereoselective synthesis of 2,3-unsaturated 1,6-oligosaccharides by means of a glycal-derived allyl epoxide and N-nosyl aziridine

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2493-2496

  Di Bussolo, Valeria ^a   Checchia, Lorenzo ^a   Romano, Maria Rosaria ^a   Pineschi, Mauro ^a   Crotti, Paolo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; AZIRIDINE DERIVATIVE; EPOXIDE; OLIGOSACCHARIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

AZIRIDINES; EPOXY COMPOUNDS; GLYCOSYLATION; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; STEREOISOMERISM;

EID: 48849087131     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800793f     Document Type: Article

References (19)

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5. For recent, effective synthesis of this kind of carbohydrates, see: (a) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428.
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10. (a) Di Bussolo, V.; Romano, M. R.; Pineschi, M.; Crotti, P. Tetrahedron 2007, 63, 2482.
11. See also: (b) Di Bussolo, V.; Romano, M. R.; Pineschi, M.; Crotti, P. Org. Lett. 2005, 7, 1299.
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13. 5c exist only as the corresponding conformer β′ (Scheme 1).
14. Crotti, P.; Di Bussolo, V.; Pomelli, C. S.; Favero, L. Theor. Chem. Acc., submitted.
15. For the preparation of 3,4-di-O-acetyl-D-glucal (9), see: Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M.; Crotti, P. Tetrahedron 2002, 58, 6069.
16. 4b
17. Trisaccharide 5 was fully characterized also as the corresponding triacetyl derivative 5-triAc (Scheme 4).
18. 5a
19. The choice of the 6-OBn protecting group on the terminal unsaturated unit of type A and B oligosaccharides was based on the assumption that its removal should occur only after functionalization of the double bond. Moreover, in type B oligosaccharides the cleavage of the benzyl ether should be carried out on the corresponding N-acetyl derivatives, rather than on the free amino group-containing compounds.