512-35-6

Usage

InChI:InChI=1/C12H10O5S2/c13-18(14,11-7-3-1-4-8-11)17-19(15,16)12-9-5-2-6-10-12/h1-10H

Upstream product

• 39083-10-8 acetone oxime-o-benzenesulfonic ester 
• 108-88-3 toluene 
• 98-11-3 benzenesulfonic acid 
• 14760-97-5 bis-benzenesulfonyl-imidazolidinetrione 
• 10028-15-6 ozone 
• 882-33-7 diphenyldisulfane 
• 26158-00-9 benzene-sulfonic acid monohydrate 
• 98-09-9 benzenesulfonyl chloride 
• 7719-09-7 thionyl chloride 
• 17882-06-3 trimethylsilyl benzenesulfonate 
• 81293-11-0 Benzolpyrosulfonsaeure-trimethylsilylester 
• 3315-16-0 silver cyanate 
• 144-62-7 oxalic acid 
• 56-23-5 tetrachloromethane 

Downstream Products

• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 80-37-5 N-(3-nitrophenyl)benzenesulfonamide 
• 7134-09-0 3,4-dihydroxybenzenesulfonic acid 
• 98-10-2 benzenesulfonamide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 227803-35-2 5-chloro-3-(phenylthio)-1H-indole 
• 54491-43-9 3-phenylthioindole 
• 1312438-43-9 dimethyl rac-2-{[bis(benzyloxy)phosphoryl]methyl}-4-[(phenylsulfonyl)oxy]pentanedioate 
• 949153-07-5 (2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoro-pyrrolidine-2-carboxamide 
• 1202-71-7 azacyclododecan-2-one 
• 32244-70-5 2.2-Dicarboxy-1-p-methoxyphenylvinylbenzolsulfonat 
• 32244-75-0 2.2-Dicarboxy-1-p-tolylvinylbenzolsulfonat 
• 488097-19-4 (3S,4S)-1-benzenesulfonyl-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol 
• 488097-18-3 (3S,4S)-1-benzenesulfonyl-9-diethoxymethyl-6-hydroxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-2,3,4,6-tetrahydro-1H-benzo[b]azocin-5-one 

Relevant academic research and scientific papers

Formal enantiospecific synthesis of (+)-FR900482

The enantiospecific synthesis of FK973, and thus a formal enantiospecific synthesis of the antitumor antibiotic (+)-FR900482, is reported. Addition of aniline 8 to chiral epoxide 9, prepared from L-vinylglycine, afforded amino alcohol 12. After protection of the aliphatic nitrogen with the 9-phenylfluoren-9-yl group, to preserve the acidic stereocenter from racemization, formation of the aziridine 14 and intramolecular condensation under basic conditions gave azocinone 15. Hydroxymethylation at the benzylic position was achieved by a process involving methylenation, epoxidation, and hydrogenolysis; the absolute stereochemistry of the resulting alcohol 23 was determined by X-ray crystallographic analysis. The hydroxyl group of 23 was carbamoylated, and the aromatic amine was deprotected electrochemically and then oxidized to give an unstable hydroxylamine that was immediately protected as acetate 26. Oxidation of 26 with DMP, followed by hydrazinolysis of the acetyl group led to spontaneous closure of the resulting N-hydroxyamino ketone to hemiketal 28, which can be considered as a fully protected precursor of FR900482 and derivatives. Acid treatment to remove the protecting groups and acetylation afforded the triacetate FK973.

Process for functionalising a phenolic compound carrying an electron-donating group

The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.

Sulfosilylation of Aromatic Hydrocarbons by Trimethylsilyl Chlorosulfonate

Aromatic hydrocarbons 2 ,6 ,8 ,9 ,13 ,16 ,18 ,19 ,22 react with trimethylsilyl chlorosulfonate (1) to give trimethylsilyl arenesulfonates 5, 7, 11, 12, 15, 23 or sulfonic acids 17, 20, 21.If trimethylsilyl sulfonates are obtained, working up of the sulfonation mixtures is possible by distillation.By hydrohalogenolysis of trimethylsilyl sulfonates 5 at 0-5 deg C anhydrous sulfonic acids 3 result.The pathways to diphenylsulfone (25a) in the reaction of benzene (2a) with 1 were investigated.In this connection we succeeded in synthesizing benzenepyrosulfonic acid (28) and trimethylsilyl benzenepyrosulfonate (29).