Synthesis of 1-Deoxy-4-thio-D-ribose starting from Thiophene-2-carboxylic acid

Author:

Altenbach Hans-Josef,Brauer David J.,Merhof Gerd F.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference22 articles.

1. According to the IUPAC-Recommendations 1996 for the nomenclature of carbohydrates (Pure Appl. Chem., 1996, 68, 1919) the naming thia- and aza-sugars should be restricted to structures where carbon, not oxygen, is replaced by a heteroatom. On the other hand the structural resemblance of a carba-sugar (correct nomenclature according to these recommendations) with the corresponding sugar and its chalcogen analogues shows that the naming “thia”- and “aza”-sugar for these systems is appropriate to differentiate from thio- and amino-sugars, where the oxygen of a hydroxy group has been replaced by a sulfur or a nitrogen atom. See also Lehmann, J. Kohlenhydrate: Chemie und Biologie; 2.ed, Thieme: Stuttgart, New York, 1996, 130.

2. Rowell, R.M.; Whistler, R.L. J. Org. Chem. 1966, 31, 1514. Ermert, P.; Vasella, A. Helv. Chim. Acta 1993, 76, 2687; and references cited therein.

3. Asymmetric synthesis of D- and L-2-deoxy-4-thioriboscs

4. Synthesis of iminothiasugar as a potential transition-state analog inhibitor of glycosyltransfer reactions

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