PRODUCTION OF SIASTATIN B, SIASTATIN B ENANTIOMER AND PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING SIASTATIN B OR SIASTATIN B ENANTIOMER

摘要

PURPOSE:To obtain the subject compound having low toxicity and useful as an antiviral agent, contraceptive agent, etc., in large quantities by oxidizing a specific compound derived from L-ribose and deprotecting the resultant product. CONSTITUTION:The objective of formula IV [(w) and (x) are (R)-configuration; (y) and (z) are (S)-configuration] is produced by (1) oxidizing the 5- hydroxymethyl group of a protected derivative of (+)-(2R or 2S, 3R, 4S, 5R)-2- acetylamino-5-(hydroxymethyl)-3,4-dihydroxy-1-azacyclohexane of formula I [R1 is H or imino-protecting group; X1 and X2 together form an OH-protecting group of formula II (R2 and R3 are H, alkyl, etc.), or cycloalkylidene; (x) and (z) is (R)-configuration; (y) is (S)-configuration; (w) is (R)-configuration when R1 is H or an imino-protecting group having lower molecular weight than acetylamino or (w) is (S)-configuration when R1 is other than those cited above] and (2) eliminating the groups R1, X1 and X2 from the produced compound of formula III [(z) is (S)-configuration].