1. The major metabolites of 3,5-di-tert.-butyl-4-hydroxytoluene (BHT) in the rat are 3,5-di-tert.-butyl-4-hydroxybenzoic acid (BHT-acid), both free (9% of the dose) and as a glucuronide (15%), and S-(3,5-di-tert.-butyl-4-hydroxybenzyl)-N-acetylcysteine. 2. The mercapturic acid does not appear to derive from the usually accepted enzyme mechanism, and may involve a non-enzymic reaction between BH...

Low-temperature ozonation (-78 degrees C) of 2-methyl-1,3-dioxolane (1a) in acetone-d6, methyl acetate, and tert-butyl methyl ether produced both the corresponding acetal hydrotrioxide (3a, ROOOH) and the hemiortho ester (2a, ROH) in molar ratio 1:5. Both intermediates were fully characterized by 1H, 13C, and 17O NMR spectroscopy, and they both decomposed to the corresponding hydroxy ester at h...

The base-induced Sommelet–Hauser (S–H) rearrangement of various types N -(pyridinylmethyl) tetraalkylammonium salts 2 to produce , -dialkyl-?-pyridinylamino acid esters 4 was investigated. For example, a treatment -(2-pyridinylmethyl) glycine tert -butyl ester-derived salt 2a with 1.2 equivalents potassium -butoxide in THF at ?40 °C gave the corresponding S–H product, 2-(dimethylamino)-2-(2-met...

deprotection of phosphate, phosphate, and sulfite esters by silica chloride is described. silica chloride is a mild, selective, and effective reagent for cleavage of benzyl and t-butyl esters of the above compounds.

p-Nitrophenyl N-butyl, N-octyl, and N-dodecyl carbamates and a newly synthesized diethyl phosphate compound were studied as potential inhibitors of the cholesteryl ester hydrolases of Fu5AH rat hepatoma cells. Whole homogenates of Fu5AH cells were used as an enzyme source for the assay of cholesteryl ester hydrolase activity. All four compounds led to marked inhibition (70-80%) of neutral chole...

Since 3,6-dichloropicolinic acid is simil8r to picloram, the method developed previously for picloram by McKone and Cotterill (1974) was examinedo This method~ like that of Pik and Hodgson, uses diazomethane for methylationo However~ the methyl ester of 3 87 acid is sufficiently volatile for losses fo occur during the final concentration stepo This report shows how tbe difficulty tan be overcom...

The pKAH-values of some substituted phenylacetic acid derivatives have been determined in the system water /dimethyl sulphoxide / 0. 11 M tetramethylammonium hydroxide. The acidity depends strongly on the polarity of the substituent in the phenyl group, Hammett p-valucs from 4.8 to 5 .8, and in the case of the same s<1bstituent decreasf's in the order nit! ik, terr-butyl ester, dimethylami<'e e...

The first total synthesis of (+/-)-actinophyllic acid (1) is reported. Key steps of this synthesis include an intramolecular oxidative coupling of ketone and malonic ester enolates and an aza-Cope-Mannich rearrangement that assembled the core structure of the natural product's unique ring system. The synthesis was accomplished from di-tert-butyl malonate in 8% overall yield by a concise sequenc...

The title compound, C(10)H(19)NO(3), is a disubstituted piperidine bearing substituents in two equatorial positions. One of the substituents is a hy-droxy group bound to nitro-gen and the second a tert-butyl ester group bound to the carbon next to the endocyclic nitro-gen. Enanti-omers of the title compound form hydrogen-bridged dimers across a center of inversion.

A novel isoxazole derivative, O-(5-isoxazolyl)-L-serine (OIS, 1), was synthesized by a Mitsunobu reaction of isoxazolin-5-one (4) with N-Boc-L-serine tert-butyl ester (5) and subsequent deprotection of the coupling product. Its structure was elucidated by spectroscopic analyses. The pharmacological activity of 1 was also examined with cloned glutamate receptors and transporters using a Xenopus ...