A Convenient Route to O-Glycosyl Lactates via Conjugate Addition to 2-Nitroglycals: Ring Closure to Novel Pyrano[2.3-b][1,4]-oxazines

Ahmed I. Khodair; Kandasamy Pachamuthu; Richard R. Schmidt

doi:10.1055/s-2003-42494

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2004(1): 53-58
DOI: 10.1055/s-2003-42494

PAPER

A Convenient Route to O-Glycosyl Lactates via Conjugate Addition to 2-Nitroglycals: Ring Closure to Novel Pyrano[2.3-b][1,4]-oxazines

Ahmed I. Khodair^b, Kandasamy Pachamuthu^a, Richard R. Schmidt*^a
^a Fachbereich Chemie, Universität Konstanz, Fach M 725, 78457 Konstanz, Germany
Fax: +49(7531)883135; e-Mail: Richard.Schmidt@uni-konstanz.de;
^b On leave from the Chemistry Department, Faculty of Education, Tanta University, Kafr El-Sheikh Branch, Kafr El-Sheikh, Egypt

Further Information

Publication History

Received 26 June 2003
Publication Date:
19 November 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Lactate esters d-2a, l-2a, and d-2b could be readily added to 3,4,6-tri-O-benzyl-2-nitro-galactal (1) and 3,4,6-tri-O-benzyl-2-nitro-glucal (4), affording exclusively α- and β-anomers with galacto- and gluco-configuration, respectively. Nitro group reduction to the amino group and ester cleavage led to compounds 6a, 6b, and 7, which can be regarded as dipeptide mimetics. For these compounds the bicyclic pyrano[2.3-b][1,4]-oxazines 8-10 were prepared via ring closure.

Key words

glycal - nitroolefin - Michael additions - glycosides - peptide mimetic - bicyclic systems - azadioxadecalines

References

1 For a review on glycosyl amino acids and carbohydrate based peptide mimetics see: Schweizer F. Angew. Chem. Int. Ed. 2002, 41: 230 ; Angew. Chem. 2002, 114, 240; and references therein

Crossref Google Scholar
Some related structures have been thus far reported as degradation products of natural compounds:
2a Stortz CA. Chermiak A. Jones RG. Treber TD. Reinhardt DJ. Carbohydr. Res. 1990, 207: 101

Google Scholar
2b Linkhardt RJ. Loganathan D. Al-Hakim A. Wang H.-M. Walenga JM. Hoppensteadt D. Fareed J. J. Red. Chem. 1990, 33: 1539

Google Scholar
3a Das J. Schmidt RR. Eur. J. Org. Chem. 1998, 1609

Crossref Google Scholar
3b Winterfeld GA. Ito Y. Ogawa T. Schmidt RR. Eur. J. Org. Chem. 1999, 1167

Crossref Google Scholar
3c Winterfeld GA. Schmidt RR. Angew. Chem. Int. Ed. 2001, 40: 2654 ; Angew. Chem. 2001, 113, 2718

Crossref Google Scholar
3d Winterfeld GA. Khodair AI. Schmidt RR. Eur. J. Org. Chem. 2003, 1009

Crossref Google Scholar
3e Khodair AI. Winterfeld GA. Schmidt RR. Eur. J. Org. Chem. 2003, 1847

Crossref Google Scholar
3f Reddy BG. Vankar YD. Tetrahedron Lett. 2003, 44: 4765

Crossref Google Scholar
4 Winterfeld GA. Das J. Schmidt RR. Eur. J. Org. Chem. 2000, 3047

Crossref Google Scholar
5 Pachamuthu K. Gupta A. Das J. Schmidt RR. Vankar YD. Eur. J. Org. Chem. 2002, 1479

Crossref Google Scholar
6 Bovin NV. Zurabyan SE. Khorlin AY. Carbohydr. Res. 1981, 87: 25

Google Scholar
7 Lemieux RU. Nagabushan TL. Gunner SW. Can. J. Chem. 1968, 46: 405

Crossref Google Scholar
8 Holzapfel CW. Marais CF. van Dyk MS. Synth. Commun. 1988, 18: 97

Crossref Google Scholar
9a Takamoto T. Sudoh R. Nakagawa T. Carbohydr. Res. 1973, 27: 135

Crossref Google Scholar
9b Sakakibara T. Tachimori Y. Sudoh R. Tetrahedron Lett. 1982, 23: 5545

Crossref Google Scholar
10 Nishimura S. Bull. Chem. Soc. Jpn. 1959, 32: 61

Crossref Google Scholar

11

This compound is commercially available.