200399-47-9Relevant articles and documents
Improved syntheses of the naturally occurring glycosidase inhibitor salacinol
Ghavami, Ahmad,Sadalapure, Kashinath S.,Johnston, Blair D.,Lobera, Mercedes,Snider, Barry B.,Pinto, B. Mario
, p. 1259 - 1262 (2003)
Improved syntheses of the naturally occurring sulfonium ion, salacinol are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 Diabetes. The synthetic strategy relies on the nucleophilic attack of 2,3,5-triO-benzyl- or 2,3,5-tri-O-p-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol at the least hindered carbon of benzylidene-protected L-erythritol-1,3-cyclic sulfate in 1,1,1,3,3,3-hexafluoro-2-propanol as solvent. The reactions are compared to those with the benzyl-protected L-erythritol-1,3-cyclic sulfate and also to those in acetone and 2-propanol. Excellent yields are obtained for the reactions with the benzylidene-protected cyclic sulfate. The synthetic route employing p-methoxybenzyl ether protecting groups is advantageous since all protecting groups in the adduct may be removed with trifluoroacetic acid to yield salacinol, thereby obviating the problematic deprotection of benzyl ethers by hydrogenolysis.
COMPOUNDS USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE SAME, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP
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, (2018/02/28)
PROBLEM TO BE SOLVED: To provide novel compounds useful for manufacturing salacinol, a method for manufacturing the compounds, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. SOLUTION: A compound represented by formula (7a) is a compound useful for manufacturing salacinol. (In the formula, R4ba is a p-toluoyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
Tanabe, Genzoh,Yoshikai, Kazuya,Hatanaka, Takanori,Yamamoto, Mizuho,Shao, Ying,Minematsu, Toshie,Muraoka, Osamu,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 3926 - 3937 (2008/02/13)
De-O-sulfonated analogs (10a, Y- = CH3OSO3 and 10b, Y- = Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y- = CH3OSO3) with l-thiosugar moiety (1,4-dideoxy-1,4-epithio-l-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent α-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of 1a against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity.