115589-79-2

Upstream product

• 630-19-3 pivalaldehyde 
• 79-42-5 2-mercaptopropanoic acid 
• 33178-96-0 (R)-thiolactic acid 
• 6398-63-6 (+/-)-trimethylsilyl 2-<(trimethylsilyl)thio>propanoate 

Downstream Products

• 92572-66-2 2-(t-butyl)-5-(1'-hydroxy-2'-cyclohexenyl)-5-methyl-1,3-dioxolan-4-one 
• 115526-70-0 (2S,5R)-2-(t-butyl)-5-methyl-5-(1-hydroxy-1'-phenylmethyl)-1,3-oxathiolan-4-one 
• 115526-70-0 (2S,4R)-2-tert-Butyl-4-(hydroxy-phenyl-methyl)-4-methyl-[1,3]oxathiolan-5-one 
• 115526-62-0 (2S,5R)-2-(t-butyl)-5-(methyl)-5-(benzyl)-1,3-oxathiolan-4-one 

Relevant academic research and scientific papers

NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND METHODS OF USE FOR SAME

The class compounds of the present invention may be represented by Formula (I), wherein X may be O, S, or N. R1 and R2 are independently either H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl

NOVEL COMPUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND METHODS OF USE FOR SAME

A pharmaceutical composition comprising a phamaceurtical diluent and a compound of formula IV wherein R21= H, C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, -CH2OR25, -C(O)R25, -CO(O)R25, -C(O)NR25R26, -CH2C(O)R25, or -CH2C(O)NHR25, where R25 and R26 are each independently H, C1-C10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing one or more halogen atoms. R22 = -OH, -OR27, -OCH2C(O)R27, -OCH2C(O)NHR27, -OC(O)R27, -OC(O)OR27, -OC(O)NHNH-R5, or -OC(O)NR27R28, where R27 and R28 are each independentlyH, C1 -C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, and where R27 and R28 can each optionally contain halogen atoms; R23 and R24, the same or different from each other, are C1-C20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. Methods of using such formulations for the treatment of cancer, to effect weight loss, to treat microbially-based infections, to inhibit neuropeptide-Y and/or fatty acid synthase, and to stimulate CPT-1.

A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds

Bismuth nitrate has been found to be an outstanding catalyst for the protection of carbonyl compounds as acetal, ketal, mixed ketal and thioketal with an excellent yield.

SYNTHESIS AND DETERMINATION OF ENANTIOMERIC EXCESSES OF NON-RACEMIC TERT-THIOLS DERIVED FROM CHIRAL SECONDARY α-MERCAPTOCARBOXYLIC ACIDS.

The optically active α-mercapto derivatives of propanoic, 3-phenylpropanoic, 2-phenylacetic, 3-methylbutanoic, 4-methylpentanoic, and (S)-3-methylpentanoic acids have been prepared.Condensation of these acids with pivalaldehyde gives 2-t-butyl-5-substituted-1,3-oxathiolanones (6); the cis geometric isomers are formed in excess and are obtained pure by crystallization.For the 5-benzyl derivative (6b) the cis arrangement for the major diastereomer was established by X-ray crystallography.These cis-disubstituted heterocycles (6), after deprotonation with lithium diisopropylamide (LDA) or lithium hexamethyldisilazide (LHMDS) and subsequent reaction with electrophiles such as alkyl halides, aldehydes, or ketones, furnish, after hydrolysis, in high enantiomeric excesses α-branched α-mercaptocarboxylic acids or esters (9).These result from an overall substitution of the proton in the α-position to the carbonyl group with retention of configuration and without racemization.This stereochemical course was established by a crystal structure determination of (2S)-8e obtained by benzylation of the enolate derived from cis-5-phenyl-1,3-oxathiolan-4-one (6c).The tert-α-mercaptocarboxylic acids are obtained optically active without employment of a chiral auxiliary.Their enantiomeric excesses were determined by esterification, conversion to diastereomeric phosphonodithionates on reaction with CH3POCl2, followed by integration of the well separated proton-decoupled (31)P NMR signals.This is apparently the first example of enantiomeric excess determinations of chiral tertiary thiols.

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).