154669-49-5

Basic information

• Product Name: 2-Oxazolidinone, 4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (4S)-
• CAS NO: 154669-49-5
• Molecular Formula: C11H13NO5S
• Molecular Weight: 271.294
• Mol File: 154669-49-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (4S)-(154669-49-5)
• EPA Substance Registry System: 2-Oxazolidinone, 4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (4S)-(154669-49-5)

Safety Data

• Hazardous Substances Data: 154669-49-5(Hazardous Substances Data)

Upstream product

• 132682-23-6 (4R)-4-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1431872-94-4 C₂₃H₂₂FN₇O₄ 
• 1431872-95-5 C₂₃H₂₂FN₇O₄ 
• 1140918-71-3 N-[(2Z)-5-tert-butyl-3-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1,3,4-thiadiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide 
• 889099-93-8 [(S)-3-(tert-butoxycarbonyl)-2-oxooxazolidin-4-yl]methyl-4-methylbenzenesulfonate 
• 365572-61-8 (4R)-4-[(4-bromophenoxy)methyl]-1,3-oxazolidin-2-one 
• 245107-02-2 Toluene-4-sulfonic acid (S)-3-methyl-2-oxo-oxazolidin-4-ylmethyl ester 
• 210635-72-6 (S)-4-[(tert-Butyl-diphenyl-silanyl)-methyl]-oxazolidin-2-one 
• 210635-70-4 (S)-4-[(Dimethyl-phenyl-silanyl)-methyl]-oxazolidin-2-one 
• 158249-50-4 4-Butyl-2-oxazolidinone 
• 161106-42-9 (R)-4-isobutyloxazolidin-2-one 
• 142758-93-8 (4R)-4-(cyclohexylmethyl)-1,3-oxazolidin-2-one 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 132682-24-7 (S)-(-)-4-iodomethyl-2-oxazolidinone 
• 157922-13-9 (R)-4-propyloxazolidin-2-one 

Relevant articles and documents

Design and synthesis of analogues of the sphingosine-1-phosphate receptor 1 agonist IMMH001 with improved phosphorylation rate in human blood

IMMH001, which is a prodrug for sphingosine-1-phosphate receptor 1 (S1P1) agonist, is converted to the active form, its monophosphate ester (S)-IMMH001-P, by sphingosine kinase 1 (SphK1) and sphingosine kinase 2 (SphK2) in vivo. In this study, we designed head-piece-modified analogues of IMMH001 based on structural information and prepared them with an efficient modular synthetic strategy. The analogues showed higher phosphorylation rates in human blood than the parent compound. These results indicated that the pro-R hydroxymethyl in the head-piece-moiety of IMMH001 prevents the pro-S hydroxymethyl from being phosphorylated by the kinase and ATP. The analogues may have better therapeutic potential.

NOVEL BENZODIOXANE-PIPERIDINE DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS FOR TREATING NEUROPSYCHIATRIC DISORDERS

The present invention concerns benzodioxane-piperidine with general formula I: wherein notably: R1 represents one or more identical or different substituent(s) on the benzene ring, each independently representing a hydrogen or halogen atom, or a C1-4 alkyl group, or a C1-4 alkoxy group or a C1-4 hydroxyalkyl group or a C1-4 alkylcarbonyl or an alkoxycarbonyl group or an OH group or an SO2R group with R alkyl, or a CN group, or a CF3 group, or an OCF 3 group; n=1, 2 or 3;m=0 or 1, andR2 represents one or more identical or different substituent(s) on the oxazolidinone or morpholinone ring, each independently representing: a hydrogen atom, a C1-4 alkyl group, or a C1-4 alkoxy group, or a C1-4 hydroxyalkyl group, or an alkylcarbonyl group, or an alkoxycarbonyl group, or an alkoxyphenyl group.

Efficient regio- And stereoselective formation of azocan-2-ones via 8-endo cyclization of α-carbamoyl radicals

The iodine-atom-transfer 8-endo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(CIO 4)2 and a bis(oxazoline) ligand, N- ethoxycarbonylsubstituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields. Similarly, the BF 3·OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields. The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-iransto 3,8-cis. Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl- substituted α-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid. In both cases, the 8-endo cyclization is always fundamentally preferred over the corresponding 7-exo cyclization. The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step. To further understand the reactivity of a-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied. The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for a-carbamoyl radicals with fixed Z-conformational transition states. As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of NH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.