Stereoselective synthesis of a C-glycoside analogue of N-Fmoc-serine β-N-acetylglucosaminide by ramberg–bäcklund rearrangement

doi:10.1016/S0960-894X(02)00104-X

Bioorganic & Medicinal Chemistry Letters

Volume 12, Issue 7, 8 April 2002, Pages 997-999

https://doi.org/10.1016/S0960-894X(02)00104-X Get rights and content

Abstract

A C-glycoside analogue of N-Fmoc-serine β-N-acetylglucosaminide 1 was synthesized stereoselectively from a sulfone derivative of serinol thio-N-acetylglucosamide 8 using a Ramberg–Bäcklund rearrangement as a key step.

Graphic

Section snippets

Acknowledgments

The NMR studies were performed in the Biochemistry NMR Facility at Johns Hopkins University, which was established by a grant from the National Institutes of Health (GM 27512) and a Biomedical Shared Instrumentation Grant (1S10-RR06262-0). This research was partly supported by the National Institutes of Health (GM 52324). We thank Dr. Shirley Wacowich-Sgarbi (Optimer Pharmaceuticals, Inc.) for critical reading of this manuscript.

References (15)

Y Ohnishi et al.
Bioorg. Med. Chem. Lett.
(2000)
P.S Belica et al.
Tetrahedron Lett.
(1998)
G Yang et al.
Org. Lett.
(1999)
F.K Griffin et al.
Tetrahedron Lett.
(1998)
A.D Campbell et al.
Chem. Commun.
(1999)
F.K Griffin et al.
Angew. Chem., Int. Ed. Engl.
(1999)
A.D Campbell et al.
Tetrahedron Lett.
(1999)
L Wells et al.
Science
(2001)
A Dondoni et al.
Chem. Rev.
(2000)
S.P Vincent et al.
J. Org. Chem.
(2000)

There are more references available in the full text version of this article.

Cited by (36)

Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones
2015, Journal of Organic Chemistry
An efficient and divergent approach to C(2)–C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO₄ and in situ generation of RuO₄ from a RuCl₃–NaIO₄ reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation–oxidation–dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.
The Ramberg-Bäcklund Rearrangement and the Eschenmoser Coupling Reaction
2014, Comprehensive Organic Synthesis: Second Edition
The present review surveys the main relevant advances on the two carbon–carbon bond forming reactions, the Ramberg–Bäcklund rearrangement (RBR) and the Eschenmoser coupling reaction (ECR), after the publication of the first edition of Comprehensive Organic Synthesis in 1991. These two subjects were combined within one chapter due to their common mechanistic feature. Both proceed via the base-induced formation of an intermediate three-membered sulfur-containing heterocycle followed by sulfur-derived extrusion. However, if episulfones (thiirane-1,1-dioxides) are involved in the case of the RBR, episulfides (thiiranes) are the transient species in the ECR. With regard to the RBR, the isolation of previously postulated episulfone intermediate as well as its various important synthetic modifications are of special interest. A number of synthetic applications have been described, including preparation of natural products and complex bioactive molecules, synthesis of conjugated dienes, enynes, and polyenes and novel electrically conducting materials; it also provides the possibility of ring enlargement of cyclic ketones. As concerning the ECR, providing a convergent method for the synthesis of vinylogous amides and carbamates, valuable synthetic intermediates, emphasis is on its application to the natural product and bioactive molecule synthesis.
A convenient and highly stereoselective method for synthesis of octahydropyrano[3,2-b]pyrrole derivatives
2013, Carbohydrate Research
Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer-intermolecular allylation reaction
2008, Tetrahedron Letters
Application of HOF·CH<inf>3</inf>CN to the synthesis of glycosyl sulfones
2008, Tetrahedron
Citation Excerpt :
Recent success in the use of KMnO4/CuSO4·5H2O26 for the oxidation of thioglycosides bearing labile acidic groups has been reported. Probably, the most frequently used reagent is m-chloroperoxybenzoic acid (m-CPBA).4,6,10,12,21 However, the low solubility of m-CPBA in dichloromethane, the frequent requirement for strict control of temperature and the difficulty in removing the by-product (m-chlorobenzoic acid) are drawbacks to its use.
Intramolecular 1,5-hydrogen atom transfer reaction promoted by phosphoramidyl and carbamoyl radicals: synthesis of 2-amino-C-glycosides
2007, Tetrahedron Letters

View all citing articles on Scopus

^†: Current address: National Institutes of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan.

View full text

Stereoselective synthesis of a C-glycoside analogue of N-Fmoc-serine β-N-acetylglucosaminide by ramberg–bäcklund rearrangement

Abstract

Section snippets

Acknowledgments

Bioorg. Med. Chem. Lett.

Tetrahedron Lett.

Org. Lett.

Tetrahedron Lett.

Chem. Commun.

Angew. Chem., Int. Ed. Engl.

Tetrahedron Lett.

Science

Chem. Rev.

J. Org. Chem.