7252-34-8

Upstream product

• 98-91-9 thiobenzoic acid 
• 55-21-0 benzamide 
• 98-91-9 thiobenzoic acid 
• 52-90-4 L-Cysteine 
• 98-88-4 benzoyl chloride 
• 52-89-1 l-cysteine hydrochloride 

Downstream Products

• 236413-32-4 N,S-dibenzoyl-L-cysteine methyl ester 
• 5673-89-2 N-benzoyl-L-cysteine dimethyl ester 

Relevant academic research and scientific papers

The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol

3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-β and -α-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the 1H NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-β-D-lyxo-hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data. Copyright (C) 2000 Elsevier Science Ltd.

Methyl esters of N-protected-O-or -S-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2 - enopyranosyl)-L-serine, -L-threonine and -L-cysteine: Synthesis and some transformations

Methyl esters of N-tosyl-O-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-L-serine (5), -L-threonine (6) and N-benzoyl-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-L -cysteine (7) have been synthesized by condensation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (1) with respective derivatives of L-serine (2), L-threonine (3) and L-cysteine (4), cis-Hydroxylation and epoxydation of 2,3-unsaturated glycopyranoside 5 afforded O-glycosyl-L-serine derivatives with α-D-manno (8, 9), 2,3-anhydro-α-D-manno (10) and 2,3-anhydro-α-D-allo (11) structures, respectively. The structure of compounds as well as conformation of the sugar residue and configuration at the anomeric centre were established on the basis of the 1H and 13C NMR (DQF-COSY, TOCSY, HMBC), IR, MS (FD) spectrometric techniques and polarimetric data.

Synthesis and properties of derivatives of 2-deoxy-2-hydroxyimino-D-arabino-hexopyranosyl-L-cysteine and -thiophenol

3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-α- and -β-D-arabino-hexopyranosides of thiophenol (3-5) as well as the methyl ester of N-benzoyl-L-cysteine (6,7) have been synthesized by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride (1) with thiophenol and the L-cysteine derivative, respectively. The glycopyranosides of thiophenol were modified at C-2 and C-3 positions to afford thiophenol derivatives with 2-deoxy-2-hydroxyamino-α-D-glucopyranosyl (13,14), 3-azido-2,3-dideoxy-2-hydroxyimmo-α-D-arabino-(8), β-D-arabino-(10), and α-D-ribo-hexopyranosyl (9) structures. The conformation of the sugar residue and configuration at the anomeric center and of the hydroxyimino group were established on the basis of the 1H, 13C, 15N NMR (DQF-COSY, TOCSY, NOESY, ROESY, HSQC, HMBC and HMBCN) spectrometric techniques and polarimetric data.

BENZOYLTHIO COMPOUNDS, THEIR PREPARATION AND THEIR USE AS DRUGS

Benzoylthio compounds of the formula I STR1 where R 1 and R. sup.3 are identical or different and are each hydrogen or C 1-C 4-alkyl, R 2 and R 4 are identical or different and are each hydrogen or C. sub.1-C 6-alkyl which is unsubstituted or substituted by hydroxyl, mercapto, C 1-C 4-alkylthio, a carboxylic ester group, carboxamido or acylamino or are each an aryl, hetaryl, arylalkylene or hetarylalkylene radical which is unsubstituted or substituted in the aryl moiety by hydroxyl, C 1-C. sub.4-alkoxy, arylalkoxy or halogen, R 1 and R 2 and/or R 3 and R. sup.4 together may furthermore be a radical--(CH 2) p--(p=2, 3, 4),--CH 2--S--CH 2--or--CH 2--C 6 H 4--CH 2--(ortho), X is NH or sulfur, m and n are identical or different and are each 0 or 1, and q is 0 or 1 where X is S, and is 0 where X is NH, and their salts with physiologically tolerated bases, their preparation, drugs containing these compounds and the use of these drugs in treating disorders.