Pseudo sugars synthesis

Barton, D H R, Augy-Dorey, S, Camara, J, DaUco, P, Delaumeny, J M, Gero, S D, Quiclet-Sire, B, Stutz, P, Synthetic methods for the preparation of basic D-pseudo-sugars and L-pseudo-sugars — synthesis of carbocyclic analogs of A-acetyl-muramyl-L-alanyl-D-isoglutamine (Mdp), Tetrahedron, 46, 215-230, 1990. 

M. Yoshikawa, N. Murakami, Y. Yokokawa, Y. Inoue, Y. Kuroda, andI. Kitagawa, Stereoselective conversion of D-glucuronolactone into pseudo-sugar, synthesis of /escudo- -i)-glucopyranose, pseudo-fS-D-glucopyranose and validamine, Tetrahedron, 50 (1994) 9619-9628. 

Sulfinylacrylate 41 has been successfully used in the enantioselective synthesis of pseudo-sugar [46, 47]. Cycloaddition of (S)-3-(2-pyridylsulfinylacrylate) (41) with furan and 3,4-dibenzyloxyfuran under Et2AlCl catalysis afforded cycloadducts 42, 43 and 44 (Equation 3.12) which were converted into pseudo-manno-pyranoses 45, 46 and 47 (Figure 3.5). 

Stick RV (1997) The Synthesis of Novel Enzyme Inhibitors and Their Use in Defining the Active Sites of Glycan Hydrolases. 187 187-213 Stutz AE, see de Raadt A (1997) 187 157-186 Stumpe R, see Kim JI (1990) 157 129-180 Suami T (1990) Chemistry of Pseudo-sugars. 154 257-283 Suppan P (1992) The Marcus Inverted Region. 153 95-130 Suzuki N (1990) Radiometric Determination of Trace Elements. 157 35-56 Tabakovic I (1997) Anodic Synthesis of Heterocyclic Compounds. 185 87-140 Takahashi Y (1995) Identification of Structural Similarity of Organic Molecules. 174 105-134 Tasi G, Palinkd I (1995) Using Molecular Electrostatic Potentid Maps for Similarity Studies. 174 45-72... 

As the Diels-Alder cyclic adduct 33 has been recognized as the most accessible starting compound for the synthesis of racemic pseudo-sugars, a resolution of 33 has been attempted to prepare enantiomeric pseudo-sugars, starting from an optically active antipode of 33. It has been revealed that 33 was readily separated into the enantiomers by using optically active a-methylbenzylamines as resolution reagents. 

All the theoretically predictable sixteen racemic pseudo-sugars have been synthesized, as well as the ten enantiomers. The most accessible starting material for the synthesis was the Diels-Alder adduct 33 of furan and acrylic acid. Furthermore, the adduct 33 was readily resolved by means of optically active a-methylbenzylamines into the two antipodes 86 and 87, which were also used for the preparation of enatiomeric pseudosugars. A chiral synthesis from true sugars was another prominent method for the preparation of the enantiomers. The remaining twenty two unknown enantiomeric pseudo-sugars will be prepared by either one of the two methods in the near future. 

Miyazaki M Master Thesis, Synthesis of enantiomeric pseudo-sugars , Keio University, 1986... 

Fabris F, Collins J et al (2009) Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem 7 2619-2627... 

Takahashi, T. et al. A New Synthetic Approach to Pseudo-Sugars by Asymmetric Diels-Alder Reaction. Synthesis of Optically Pure Pseudo-f3-D-mannopyranose, I-Amino-I-deoxypseudo-a-D-manno-pyranose and Pseudo-a-L-mannopyranose Derivatives. 3.1 1990 [182]... 

Ogawa S, Tsunoda H (1992) Pseudo-sugars. XXXI. New synthesis of 2-amino-5a-carba-2-deoxy-a-DL-glucopyranose and its transformation into valien-amine and valiolamine analogues. Liebigs Ann Chem 6 637-641... 

Ogawa, S, Uematsu, Y, Yoshida, S, Sasaki, N, Suami, T, Pseudo-sugars. 18. Synthesis and sweetness of pseudo-beta-D and L-fmctopyranose, J. Carbohydr. Chem., 6, 471-478, 1987. 

Yoshikawa, M, Murakami, N, Inoue, Y, Hatakeyama, S, Kitagawa, I, A new approach to the synthesis of optically-active pseudo-sugar and pseudo-nucleoside — syntheses of pseudo-alpha-D-arabinofur-anose, (- -)-cyclaradine, and (-l-)-l-pseudo-beta-D-arabinofuranosyliiracil from D-arabinose, Chem. Pharm. Bull, 41, 636-638, 1993. 

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