PURPOSE: To provide a method to efficiently obtain the subject compound useful for medicines, agricultural chemicals, etc., in a high yield by reacting a compound obtained by adding an iodine group and an acyloxy group to a double bond of anhydrodideoxythreohexoenopyranose under specific conditions.
CONSTITUTION: In a compound of formula II (R is an acyl) obtained by adding an iodine group at α configuration to 4-position of the double bond of 1,6- anhydro-3,4-dideoxy-β-D-threo-hexo-3-enopyranose of formula I and adding an acyloxy ion at β configuration to 3-position of the double bond of the compound of formula I to carry out trans-addition, the acyloxy group is hydrolyzed in the presence of a base to afford a compound of formula III having an oxirane ring at β configuration. The ring of this compound is reductively opened and the hydroxyl group is protected to give a compound of formula IV (R1 is a protecting group of hydroxy group). The 1,6-anhydro bond and the protecting group of the hydroxy group of the compound of formula IV are hydrolyzed with an acid to provide the compound of formula V.
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EBATA TAKASHI
KOSEKI YUKIFUMI
OKANO KOJI
KAWAKAMI HIROSHI
MATSUSHITA HAJIME
