SYNTHESIS OF O-(4,6-DI-HYDROXY-2,3-DI-O-METHYL-ALFA-D-GLUCOPYRANOSYL)-(1->4)-O-(2,3,6-TRI-O-METHYL-ALFA-D-GLUCOPYRANOSYL)-(1->4)-O-(2,3,6-TRI-O-METHYL-1-

HESTY PARBUNTARI, Drs. Bambang Purwono, M.Sc., Ph.D. ; Dr. Respati T. Swasono, M.Phil.

2016 | Tesis | S2 Ilmu Kimia

Turunan maltotriosa (1-6) telah disintesis. Turunan maltotriosa 6 merupakan prekursor dari analog beta-siklodekstrin 7. Ada enam langkah untuk mensintesis turunan maltotriosa 6, yakni O-asetilasi, tioglikosidasi, de-asetilasi, benzilidasi, O-metilasi, dan de-benzilidasi. Turunan maltotriosa 1 disintesis dengan natrium asetat anhidrat dan asam asetat anhidrat berdasarkan metode Sakairi dan Kazuhara. Turunan maltotriosa 2 disintesis dengan menggunakan 1-dodekanatio dan boron triflorida dietil eter. Turunan maltotriosa 3 disintesis dengan natrium metoksida dalam metanol 28%. Turunan maltotriosa 4 disintesis dengan asam kamfor sulfonat dan benzaldehida dimetil asetal. Turunan maltotriosa 5 disintesis dengan dimetil sulfat dan natrium hidrida 60%. Turunan maltotriosa 6 disintesis dengan asam asetat 80%. Struktur produk dianalisis dengan Fourier Transform Infrared (FTIR) Specstroscopy, 1H-, 13C- NMR, COSY NMR, dan ESI Mass Spectroscopy. Hasil penelitian menunjukkan bahwa O-asetilasi menghasilkan turunan maltotriosa 1 (95%), tioglikosidasi menghasilkan turunan maltotriosa 2 (54%), de-asetilasi menghasilkan turunan maltotriosa 3 (97%), O-benzilidasi menghasilkan produk campuran dari turunan maltotriosa 4, O-metilasi menghasilkan turunan maltoriosa 5 (46%), dan de-benzilidasi menghasilkan turunan maltotriosa 6 (85%).

Maltotriose derivatives (1-6) have been synthesised. Maltotriose derivative 6 is a precursor of beta-cyclodextrin analogue 7. There were six steps to synthesise maltotriose derivative 6, i.e. O-acetylation, thioglycosidation, de-acetylation, benzylidation, O-methylation, and de-benzylidation. Maltotriose derivative 1 was synthesised with anhydrous sodium acetate and acetic anhydride based on Sakairi and Kazuhara method. Maltotriose derivative 2 was synthesised with 1-dodecanethiol and boron triflouride diethyl etherate. Maltotriose derivative 3 was synthesised with sodium methoxide in methanol 28%. Maltotriose derivative 4 was synthesised with camphor sulfonic acid and benzaldehyde dimethyl acetal. Maltotriose derivative 5 was synthesised with dimethyl sulfate and sodium hydride 60%. Maltotriose derivative 6 was synthesised with acetic acid 80%. The product structures were analysed by Fourier Transform Infrared (FTIR) Specstroscopy, 1H-, 13C-NMR, COSY NMR, and ESI Mass Spectroscopy. The result showed that O-acetylation reaction produced maltotriose derivative 1 (95%), thioglycosidation reaction produced maltotriose derivative 2 (54%), de-acetylation reaction produced maltotriose derivative 3 (97%), O-benzylidation reaction produced a mixture of maltotriose derivatives 4, O-methylation reaction produced maltotriose derivative 5 (46%) and de-benzylidation reaction produced maltotriose derivative 6 (85%).

Kata Kunci : synthesis, maltotriose, derivative, cyclodextrin, analogue