A Stereoselective Synthesis of N-β-d-Glycosyl Amides by a Ritter-type Reaction

Xuezheng Song; Rawle I. Hollingsworth

doi:10.1055/s-2006-958417

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-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2006(20): 3451-3454
DOI: 10.1055/s-2006-958417

LETTER

A Stereoselective Synthesis of N-β-d-Glycosyl Amides by a Ritter-type Reaction

Xuezheng Song^a, Rawle I. Hollingsworth*^a,b
^a Department of Chemistry and Biochemistry, Michigan State University, East Lansing, MI 48824, USA
^b Department of Molecular Biology, Michigan State University, East Lansing, MI 48824, USA
Fax: +1(517)3539334; e-Mail: rih@cem.msu.edu;

Further Information

Publication History

Received 16 February 2006
Publication Date:
08 December 2006 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A facile stereoselective synthesis of protected N-glycosyl amides is reported. Peracetates or perpivaloates of monosaccharides with gluco-, galacto- and manno-configurations react with acetonitrile in a Ritter-like fashion under acidic condition. The stereoselectivity of this anomeric Ritter-type reaction strongly favors β-anomers of N-d-glycosyl amides regardless of the configurations of the sugars.

Key words

Ritter reaction - amidation - glycosyl amide

References

1 Arsequell G. Valencia G. Tetrahedron: Asymmetry 1999, 10: 3045

Crossref Search in Google Scholar
2 Grogan MJ. Pratt MR. Marcaurelle LA. Bertozzi CR. Annu. Rev. Biochem. 2002, 71: 593

Crossref Search in Google Scholar
3a Ratcliffe AJ. Fraser-Reid B. J. Chem. Soc., Perkin Trans. 1 1989, 1805

Crossref
3b Ratcliffe AJ. Konradsson P. Fraser-Reid B. Carbohydr. Res. 1991, 216: 323

Crossref Search in Google Scholar
3c Handlon AL. Fraser-Reid B. J. Am. Chem. Soc. 1993, 115: 3796

Crossref Search in Google Scholar
3d Ratcliffe AJ. Mootoo DR. Andrews CW. Fraser-Reid B. J. Am. Chem. Soc. 1989, 111: 7661

Crossref Search in Google Scholar
3e Nair LG. Fraser-Reid B. Szardenings AK. Org. Lett. 2001, 3: 317

Crossref Search in Google Scholar
4a Likhoshertov LM. Novikova VA. Dervitskaja VA. Kochetkov NK. Carbohydr. Res. 1986, 46: C1

Crossref Search in Google Scholar
4b Lubineau A. Auge J. Drouillat B. Carbohydr. Res. 1995, 266: 211

Crossref Search in Google Scholar
4c Danishefsky SJ. Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 35: 1380

Crossref Search in Google Scholar
4d Dorsey AD. Barbarow JE. Trauner D. Org. Lett. 2003, 5: 3237

Crossref Search in Google Scholar
4e Damkaci F. DeShong P. J. Am. Chem. Soc. 2003, 125: 4408

Crossref Search in Google Scholar
4f Nicolaou KC. Snyder SA. Nalbandian AZ. Longbottom DA. J. Am. Chem. Soc. 2004, 126: 6234

Crossref Search in Google Scholar
4g Tanaka H. Iwata Y. Takahashi D. Adachi M. Takahashi T. J. Am. Chem. Soc. 2005, 127: 1630

Crossref Search in Google Scholar
5a Pleuss N. Kunz H. Angew. Chem. Int. Ed. 2003, 42: 3174

Thieme Connect Search in Google Scholar
5b Pleuss N. Kunz H. Synthesis 2005, 122

Thieme Connect
6a Pavia AA. Ung-Chhun SA. Durand J.-L. J. Org. Chem. 1981, 46: 3158

Thieme Connect Search in Google Scholar
6b Noort D. van der Marel GA. Mulder GJ. van Boom JH. Synlett 1992, 224

Thieme Connect
6c Jiménez Blanco JL. Rubio EM. Ortiz Mellet C. García Fernández JM. Synlett 2004, 2230

Thieme Connect
7a Schweizer F. Lohse A. Otter A. Hindsgaul O. Synlett 2001, 1434
7b Lohse A. Schweizer F. Hindsgaul O. Comb. Chem. High Throughput Screening 2002, 5: 389

Search in Google Scholar