Add time:08/10/2019         Source:sciencedirect.com

The previously reported6, unequivocal synthesis of the title compound (5a) afforded a general method for the preparation of 4-substituted 4-thiazoline-2-thiones derived from fully acetylated α-halo ketoses. Such use of the α-halo ketoses (1b) or (2b) (as outlined in MethodI of the Scheme) led to the crystallineL enantiomorph (5b) that, on cocrystallization with5a, gave theDL form (5c). By use of the α-bromo ketoses (1d-1f), further application of the method yielded amorphous, highly soluble,D-xylo,L-xylo (crude), andD-gluco analogs5d-5f, respectively. Agalacto-1,4-bis-(4-thiazoline-2-thione) analog (5g), similarly obtained from the α-bromo ketose (1g), was crystalline, high-melting, and highly insoluble. By a modification of the procedure (Method II), treatment of the α-bromo ketoses (1h-1i) with the dithiocarbamic acid salts, derived from carbon disulfide and methylamine or 4-aminobutyric acid, led to the crystalline 4-thiazoline-2-thiones (5h-5i), respectively, that are also substituted at theN-hetero atom. Compounds intermediate in these syntheses are reported.

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