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Synthesis is described on 6-O-[2-deoxy-2-((R)-3-hydroxytetradecanoylamino)-6-O-tetradecanoyl-β-D-glucopyranosyl]-2-deoxy-2-((R)-3-hydroxytetradecanoylamino)-3,4-di-O-tetradecanoyl-D-glucopyranose which corresponds to the phosphate-less lipid A structure of Salmonella-type bacterial endotoxin.

A novel method was established for the determination of true optical purity of amino acid residues in peptides. Hydrolysis in deuterium chloride followed by mass fragmentographic detection enables very accurate analysis without disturbance by racemization in the hydrolysis procedure.

α-Glycosyl phosphates and 4-phosphates of N-acylglucosamine derivatives were prepared in high yields via the reaction of corresponding O-lithium salts with dibenzyl or diphenyl phosphorochloridate at low temperature.

The title compound was synthesized and identified with a partial hydrolysis product from natural streptothricin. This work confirmed the presence of the proposed glycosyl guanidine structure in the antibiotic and established a method for its preparation.

The enantioface-differentiating hydrogenation of methyl 3-oxotetradecanoate over (R,R)-tartaric acid-NaBr-modified nickel gave methyl (R)-3-hydroxytetradecanoate(III) in 85% e.e.. After HI was converted to dicyclohexylammonium salt of 3-hydroxytetradecanoic acid (I), the salt was recrystallized three times from acetonitrile and was then treated with acid to give optically pure (R)-I in a good yield.

1-Succinimidyl esters of various aliphatic acids and amino acids were reduced with sodium borohydride in tetrahydrofuran to the corresponding alcohols under mild conditions in fairly good yields. The facile reaction offers a convenient method for the preparation of alcohols from carboxylic acids, and can be effectively applied to a selective conversion of an appropriate carboxyl group to a hydroxymethyl group in the presence of other functional groups.