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Mono- and bis-sulfonamide derivatives of l-lysine were obtained for the first time by the reaction of methyl lysinate with ethyl 12-sulfodehydroabietate. Sulfonamides containing an additional sulfonamide or amide group in the α-position of lysine were synthesized by involving camphor-10-sulfonyl chloride, as well as isonicotinoyl, benzoyl, and α-naphthoyl chlorides in the reaction. The corresponding hydrazide and acid were also prepared by the modification of the ester group of N-dehydroabietane-derived methyl lysinate. [ABSTRACT FROM AUTHOR]

A series of asymmetric disulfides was obtained in yields of 38–50% by the co-oxidation of a mixture of diterpene abietane-derived thiols and thiols synthesized from protected monosaccharides with galacto-, fructo-, and glucopyranose and ribofuranose fragments. After removal of the acetyl protection in the disulfide containing 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose and dehydroabietane moieties, a disulfide with free glucose hydroxyl groups was obtained in a yield of 94%. [ABSTRACT FROM AUTHOR]

Optically active derivatives of 3,4-dihydropyrimidin-2(1H)-one have been synthesized on the basis of myrtenal and methyl 2,3-O-isopropylidene-α-L-erythro-pentodialdo-1,4-furanoside in 45 and 50% yields, respectively, and subjected to stereoselective chlorination with chlorine dioxide, which afforded a series of mono-, di-, and trichloro derivatives in up to 98% yield. [ABSTRACT FROM AUTHOR]

A number of thioglycosides derived from benzoylated glucopyranose and nitrogen-containing heterocyclic thiols have been synthesized in up to 98% yield, and benzoyl protecting groups have been removed from the glycoside with a 3-phenyl-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl fragment. [ABSTRACT FROM AUTHOR]

The reaction of 12-(chlorosulfonyl)dehydroabietic acid ethyl ester with methyl esters of amino acids (glycine, methionine, leucine, glutamic acid, tyrosine, proline, and histidine) afforded previously unknown sulfonamides which were selectively converted to amino acid hydrazides without involving the ethyl ester moiety of dehydroabietic acid. In the reaction with glutamic acid dimethyl ester, the corresponding dihydrazide was obtained. 12-(Chlorosulfonyl)dehydroabietic acid ethyl ester reacted with cystine dimethyl ester to give bis-sulfonamide as the only product, while the same reaction carried out in acetone-containing medium was accompanied by cleavage of the cystine S–S bond with the formation of acetone dithioacetal. Treatment of the bis-sulfonamide and thioketal with chlorine dioxide selectively produced the same chlorosulfonyl derivative as a result of oxidation of the disulfide or thioketal moiety [ABSTRACT FROM AUTHOR]