Novel diMmercaptoisotrithione (DMIT) and tetrathiafulvalene (TTF) with glucose units: Synthesis and characterization

• Main Author: Galian, Richard Anthony F.
• Format: text
• Language: English
• Published: Animo Repository 2000
• Subjects: Tetrathiafulvalene; Sugar—Derivatives; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_masteral/6293; https://animorepository.dlsu.edu.ph/context/etd_masteral/article/13381/viewcontent/TG07378b_Redacted.pdf
• Institution: De La Salle University

Symmetrical dimercaptoisotrithione (DMIT)- and tetrathiafulvalene (TTF)- sugar derivatives attached to C-6 of the sugar moieties were synthesized (7, 8a-b). The synthesis of the DMIT-sugar derivative (7) involved the reaction of bis(tetraethylammonium)bis(1,3-dithiole-2-thione-4,5-dithiolato)zincate(II) with 1,2,3,4-tetra-o-acetyl-6-deoxy-6-iodo-a-d-glucopyranoside in dimethyl formamide. Harsh coupling conditions with thriethyl phosphite [P(OEt)3] gave negative results for the synthesis of symmetrical TTF-sugar derivative (8)a. This problem was circumvented by using tetra(cyanoethylthio)tetrathiafulvalene (TCT-TTF) (4) to generate the tetrathiolate (TTFTT) nucleophile for the synthesis of (8a), followed by its hydrolysis to produce (8b). 1H-, 13C-, 13C-DEPT and HMQC NMR, FTIR and mass spectral data were obtained for structure elucidation.