Date of Publication

1-2000

Document Type

Master's Thesis

Degree Name

Master of Science in Chemistry

Subject Categories

Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Gerardo C. Janairo

Defense Panel Chair

Glenn V. Alea

Defense Panel Member

Eric L. De Leon
Aristea V. Bayquen

Abstract/Summary

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.

Abstract Format

html

Language

English

Format

Print

Accession Number

TG07378

Keywords

Tetrathiafulvalene; Sugar—Derivatives

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Embargo Period

9-6-2022

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