First synthesis of 4,5-O-isopropylidene-6-thio-d-galactono-1,6-lactone as a precursor of d-galactothioseptanose |
| |
| Affiliation: | 1. Laboratory of Organometallics, Department of Chemistry, Universidad Técnica Federico Santa María, Avenida España N° 1680, Valparaíso, Chile;2. Department of Chemistry, Faculty of Science, Universidad de Chile, Las Palmeras N° 3425, Ñuñoa, Santiago, Chile;3. School of Medicine, Centro de Investigaciones Biomédicas (CIB), Universidad de Valparaíso, Avenida Hontaneda N° 2664, Valparaíso, Chile;1. Inorganic Chemistry Department, University of Yaoundé I, B.P. 812, Yaoundé, Cameroon;2. Institute of Condensed Matter and Nanosciences (IMCN), Université catholique de Louvain, Croix du Sud 1, B-1348, Louvain-la-Neuve, Belgium;3. Materia Nova ASBL, Rue de l’Epargne 56, B-7000 Mons, Belgium;4. Materials Science Department, University of Mons, 20, Place du parc, 7000, Mons, Belgium;5. Chemistry Department, Higher Teacher Training College, University of Yaounde I, B.P. 47, Yaoundé, Cameroon;1. Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, United States;2. The Polymer Program, University of Connecticut, 97 North Eagleville Road, Storrs, CT 06269, United States;1. Department of Analytical Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Šrobárova 2, 041 80 Košice, Slovak Republic;2. Institute of Recycling Technologies, Faculty of Metallurgy, Technical University of Košice, Letná 9, 042 00 Košice, Slovak Republic |
| |
| Abstract: | Displacement of the bromide group in methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-d-galactonate 7, with potassium thioacetate gave methyl 6-(S)-acetyl-2,3:4,5-di-O-isopropylidene-6-thio-d-galactonate 8 in quantitative yield. Regioselective removal of the 2,3-ketal protecting group afforded methyl 6-(S)-acetyl-4,5-O-isopropylidene-6-thio-d-galactonate 11 in 70% yield. Saponification of compound 11 gave the 6-(S)-4,5-O-isopropylidene-6-thio-d-galactonic acid 12 in quantitative yield. Treatment of 12 with DIC/HOBt as coupling reagents gave, after cyclisation; the target compound: 4,5-O-isopropylidene 6-thio-d-galactono-1,6-lactone 13 in 49% yield. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
