An Easy Route to 2‐Amino‐β‐C‐Glycosides by Conjugate Addition to 2‐Nitroglycals

2-Nitroglycals were found to undergo conjugate addition with a variety of stabilized soft carbanions. The Michael adducts from galactal derivatives were converted into bicyclic lactams.

[1]  U. Flörke,et al.  Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids. , 2001, Organic letters.

[2]  R. Bittman,et al.  Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids. , 2001, Organic letters.

[3]  R. Schmidt,et al.  Synthesis of a C-Glycoside Analog of the Tumor-Associated Tn Antigen , 2001 .

[4]  T. Gallagher,et al.  Radical-mediated synthesis of α- C -glycosides based on N -acyl galactosamine , 2000 .

[5]  A. Marra,et al.  Methods for anomeric carbon-linked and fused sugar amino Acid synthesis: the gateway to artificial glycopeptides. , 2000, Chemical reviews.

[6]  R. Schmidt,et al.  Convenient Synthesis of Nucleosides of 2-Deoxy-2-nitro-D-galactose andN-Acetyl-D-galactosamine , 2000 .

[7]  A. Marra,et al.  General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines , 2000 .

[8]  F. Nicotra,et al.  Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine , 2000 .

[9]  A. Schäfer,et al.  Synthesis of novel donor mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as potential transferase inhibitors. , 2000, The Journal of organic chemistry.

[10]  Yukishige Ito,et al.  A Novel and Efficient Route towards α‐GalNAc‐Ser and α‐GalNAc‐Thr Building Blocks for Glycopeptide Synthesis , 1999 .

[11]  Juan Xie,et al.  ALKYLIDENATION OF SUGAR LACTONES AND FURTHER TRANSFORMATION TO C-GLYCOSIDES , 1999 .

[12]  Carol M. Taylor.  Glycopeptides and glycoproteins: Focus on the glycosidic linkage , 1998 .

[13]  R. Linhardt,et al.  Recent Advances in Stereoselective C-Glycoside Synthesis , 1998 .

[14]  R. Schmidt,et al.  Convenient Glycoside Synthesis of Amino Sugars: Michael‐Type Addition to 2‐Nitro‐D‐galactal , 1998 .

[15]  J. Cui,et al.  Stereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure , 1998 .

[16]  T. Fuchss,et al.  Synthesis of the C-Analog of 2-Acetylamino-2-deoxy-β-d-glucopyranosyl l- and d-Serine , 1998 .

[17]  T. Skrydstrup,et al.  First synthesis of a C-glycoside anologue of a tumor-associated carbohydrate antigen employing samarium diiodide promoted C-glycosylation , 1998 .

[18]  T. Fuchss,et al.  A General Method for the Synthesis of C‐Glycosides of Nojirimycin , 1997 .

[19]  H. Kessler,et al.  STEREOSELECTIVE SYNTHESIS OF A C-GLYCOSIDIC ANALOG OF N-GLUCOASPARAGINE , 1997 .

[20]  H. Kessler,et al.  Stereoselektive Synthese eines C‐glycosidischen Analogons des N‐Glucoasparagins , 1997 .

[21]  M. Ihara,et al.  A MILD OXIDATIVE TRANSFORMATION OF NITRO COMPOUNDS INTO KETONES BY TETRAPROPYLAMMONIUM PERRUTHENATE , 1997 .

[22]  L. Petruš,et al.  Synthesis of 2-(β-d-glycopyranosyl)nitroethenes and -nitroethanes via aldehydo derivatives , 1996 .

[23]  R. Schmidt,et al.  Glycosyl Imidates, 76. Synthesis of Aryl C‐Glycosides of Glucosamine , 1996 .

[24]  C. Bertozzi,et al.  Synthesis of beta-C-Glycosides of N-Acetylglucosamine via Keck Allylation Directed by Neighboring Phthalimide Groups. , 1996, The Journal of organic chemistry.

[25]  Yuan-chuan Lee,et al.  Chemoenzymatic synthesis of a high-mannose-type N-glycopeptide analog with C-glycosidic linkage , 1996 .

[26]  A. Wei,et al.  Biological Evaluation of Rationally Modified Analogs of the H-Type II Blood Group Trisaccharide. A Correlation between Solution Conformation and Binding Affinity , 1995 .

[27]  M. Martín-Pastor,et al.  Experimental and theoretical evidences of conformational flexibility of C-glycosides. NMR analysis and molecular mechanics calculations of C-lactose and its O-analogue , 1995 .

[28]  A. Veyrières,et al.  Synthesis of C-Glycosylacetylenes: Applications to the 2-Azidosugars , 1994 .

[29]  R. Hollingsworth,et al.  Synthesis of C-glycosides of N-acetylglucosamine by direct alkylation of 2-amino-2-deoxy-2,3,4,6-tetra-O-acetyl glucopyranosyl chloride , 1994 .

[30]  A. Veyrières,et al.  Synthesis of α-C-glycopyranosides of D-galactosamine and D-glucosamine via iodocyclization of corresponding glycals and silver tetrafluoroboranuidepromoted alkynylation at the anomeric centre , 1994 .

[31]  C. Bertozzi,et al.  The synthesis of 2-azido C-glycosyl sugars , 1992 .

[32]  M. Postema.  Recent developments in the synthesis of C-glycosides , 1992 .

[33]  F. Nicotra,et al.  A new procedure for the synthesis of D-glucosamine α-C-glycosides , 1989 .

[34]  K. Sandhoff,et al.  Diastereoselektive synthese von funktionalisierten C-α- und -β-glykosylderivaten der 2-acetamido-2-desoxy-d-glucose☆ , 1987 .

[35]  T. D. Inch.  Formation of convenient chiral intermediates from carbohydrates and their use in synthesis , 1984 .

[36]  A. Vasella,et al.  Deoxy‐nitrosugars. 6th communication. Stereoelectronic control in the reductive denitration of tertiary nitro ethers. A synthesis of ‘C‐glycosides’ , 1983 .

[37]  J. Montreuil.  Primary structure of glycoprotein glycans: basis for the molecular biology of glycoproteins. , 1980, Advances in carbohydrate chemistry and biochemistry.

[38]  S. Kornfeld,et al.  Comparative aspects of glycoprotein structure. , 1976, Annual review of biochemistry.

[39]  S. Hanessian,et al.  Synthesis of naturally occurring C-nucleosides, their analogs, and functionalized C-glycosyl precursors. , 1976, Advances in carbohydrate chemistry and biochemistry.

[40]  S. Nishimura.  Raney Nickel and Platinized Rany Nickel with Higher Catalytic Activities , 1959 .