26137-70-2

Upstream product

• 14754-44-0 isocyanatosulfuric acid 2,6-dimethyl-phenyl ester 
• 125672-20-0 F-hexyl-1 diisopropylamino-2 ethanol 
• 99679-24-0 F-octyl-1 diisopropylamino-2 ethanol 
• 576-26-1 2.6-dimethylphenol 
• 1400942-09-7 2,6-dimethylphenyl 2-methyl-1H-imidazole-1-sulfonate 
• 1400942-24-6 2,6-dimethylphenyl bis(4-methoxybenzyl)sulfamate 
• 1400942-29-1 2,6-dimethylphenyl bis(2,4-dimethoxybenzyl)sulfamate 
• 92007-52-8 N-chlorosulfonylcarbamate de 2,6-dimethylphenyle 
• 35374-24-4 Chlorosulfuric acid 2,6-dimethyl-phenyl ester 

Relevant academic research and scientific papers

Efficacious N-protection of O-aryl sulfamates with 2,4-dimethoxybenzyl groups

Sulfamates are important functional groups in certain areas of current medicinal chemistry and drug development. Alcohols and phenols are generally converted into the corresponding primary sulfamates (ROSO2NH 2 and ArOSO2NH2, respectively) by reaction with sulfamoyl chloride (H2NSO2Cl). The lability of the O-sulfamate group, especially to basic conditions, usually restricts this method to a later stage of a synthesis. To enable a more flexible approach to the synthesis of phenolic O-sulfamates, a protecting group strategy for sulfamates has been developed. Both sulfamate NH protons were replaced with either 4-methoxybenzyl or 2,4-dimethoxybenzyl. These N-protected sulfamates were stable to oxidising and reducing agents, as well as bases and nucleophiles, thus rendering such masked sulfamates suitable for multi-step synthesis. The protected sulfamates were synthesised by microwave heating of 1,1′-sulfonylbis(2-methyl-1H-imidazole) with a substituted phenol to give an aryl 2-methyl-1H-imidazole-1-sulfonate. This imidazole-sulfonate was N-methylated by reaction with trimethyloxonium tetrafluoroborate, which enabled subsequent displacement of 1,2-dimethylimidazole by a dibenzylamine (e.g. bis-2,4-dimethoxybenzylamine). The resulting N-diprotected, ring-substituted phenol O-sulfamates were further manipulated through reactions at the aryl substituent and finally deprotected with trifluoroacetic acid to afford a phenol O-sulfamate. The use of 2,4-dimethoxybenzyl was particularly attractive because deprotection occurred quantitatively within 2 h at room temperature with 10% trifluoroacetic acid in dichloromethane. The four key steps in the protocol described [reaction of 1,1′-sulfonylbis(2-methyl-1H-imidazole) with a phenol, methylation, displacement with a dibenzylamine and deprotection] all proceeded in very high yields.

A novel class of antihyperlipidemic agents with low density lipoprotein receptor up-regulation via the adaptor protein autosomal recessive hypercholesterolemia

We have previously reported compound 2 as a inhibitor of acyl-coenzyme A:cholesterol O-acyltransferase (ACAT) and up-regulator of the low density lipoprotein receptor (LDL-R) expression. In this study we focused on compound 2, a unique LDL-R up-regulator,

NOVEL SULFONAMIDE DERIVATIVE

A compound of the formula (1): wherein m, n and p is independently an integer of 0 to 4 with the proviso that 3 a?| m + n a?| 8; X is the formula: NR4, etc.; R1, R3 and R4 are a substituted or unsubstituted aryl group, etc.; R2 is a hydrogen atom, etc.; a, b, c, d, e and f are a hydrogen atom or a substituted or unsubstituted alkyl group, etc.; Y is the formula: -SO2-, etc.; and Z is an oxygen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt of the same has an activity of potentiating an expression of a low density lipoprotein receptor and thus is useful as an agent for treating hyperlipidemia or arteriosclerosis.

The action of F-alkylated (alkylamino)ethanols on alkoxy- and aroxy-sulfonyl isocyanates

The action of F-alkylated (alkylamino)ethanols on alkoxy- and aroxy-sulfonyl isocyanates allowed the preparation of the corresponding carbamates. The reaction occurred rapidly with good yields.

SYNTHESES A L'AIDE D'HETEROCUMULENES. 4. Action L'Isocyanate De Chlorosulfonyle Sur les Phenols Encombres

The synthesis of the N-chlorosulfonylcarbamates derived from seven hindered phenols is described, as well as their hydrolysis giving a high yield of the corresponding simple carbamates, the selective substitution of their chlorine atom by the anilino radi