93367-10-3

Basic information

• Product Name: 1,3-Dioxolane, 2,2-dimethyl-4-(2S)-oxiranyl-, (4S)-
• Synonyms: 1,3-Dioxolane, 2,2-dimethyl-4-oxiranyl-, [S-(R*,R*)]-
• CAS NO: 93367-10-3
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Mol File: 93367-10-3.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 174.2±25.0 °C (760 mmHg)
• Density: 1.133±0.06 g/cm3 (20 °C, 760 mmHg)
• CAS DataBase Reference: 1,3-Dioxolane, 2,2-dimethyl-4-(2S)-oxiranyl-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolane, 2,2-dimethyl-4-(2S)-oxiranyl-, (4S)-(93367-10-3)
• EPA Substance Registry System: 1,3-Dioxolane, 2,2-dimethyl-4-(2S)-oxiranyl-, (4S)-(93367-10-3)

Safety Data

• Hazardous Substances Data: 93367-10-3(Hazardous Substances Data)

Upstream product

• 91274-05-4 (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 
• 128142-59-6 Naphthalene-2-sulfonic acid (S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester 
• 136233-07-3 (+)-1-O-acetyl-3,4-O-isopropylidene-L-erythritol 
• 57302-79-1 (3-hydroxymethyl-oxiranyl)-methanol 
• 116-11-0 2-Methoxypropene 
• 128056-99-5 (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 
• 136136-26-0 (-)-4-O-(t-butyldiphenylsilyl)-1,2-O-isopropylidene-D-erythritol 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 1379602-81-9 (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid sodium salt 
• 58650-93-4 2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid 
• 126946-53-0 ethyl (2R,3S)-3,4-O-isopropylidene-2-p-toluenesulfonyl-3,4-dihydroxybutanoate 
• 136136-24-8 ((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl butanoate 
• 136136-22-6 ((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate 
• 114185-09-0 (2S,3R)-1,2-isopropylidenedioxy-butan-3,4-diol 

Downstream Products

• 114185-10-3 (2S,3S)-1,3-O-dibenzylbutane-1,2,3-triol 
• 410095-16-8 (R)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-3-yn-1-ol 
• 1293966-41-2 C₁₉H₂₄ClNO₅ 
• 1293966-66-1 C₂₀H₂₆ClNO₅ 
• 1293966-80-9 C₅₉H₉₇ClO₁₃Si 
• 1293966-55-8 C₆₅H₁₁₁ClO₁₃Si₂ 
• 1384244-51-2 C₁₆H₂₄O₄ 
• 130550-65-1 (S)-4-((R)-1-(benzyloxy)allyl)-2,2-dimethyl-1,3-dioxolane 
• 104322-68-1 (2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde 
• 1418112-80-7 N-(6-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)-2-(4-fluorobenzyl-thio)pyrimidin-4-yl)-3-methylazetidine-1-sulfonamide 
• 1418112-79-4 4-chloro-6-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)-2-(4-fluorobenzylthio)pyrimidine 
• 392250-82-7 (S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxybenzyloxy)-propan-1-ol 
• 392250-83-8 (S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-propionaldehyde 

Relevant articles and documents

An improved synthesis of the C15-C28 fragment of laulimalide

The C15-C28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,20-diol stereochemistry originates in starting material 7 and the side chain was appended using a Kocienski-modified Julia coupling.

Enantioselective synthesis of fatty acid amide hydrolase inhibitors with 1, 3-disubstituted butan-2-one scaffold

Fatty acid amide hydrolase is a key enzyme in the inactivation of the analgesic and anti-inflammatory endocannabinoid anandamide. Previously, the chiral compound 1-(1H-benzotriazol-1-yl)-3-(4-phenylphenoxy)butan-2-one was identified as a potent inhibitor of fatty acid amide hydrolase and is therefore of interest as a potential agent against pain and inflammation. Two different approaches for the enantioselective synthesis of fatty acid amide hydrolase inhibitors with a 1, 3-disubstituted butan-2-one scaffold were carried out. The first one uses the chiral epoxide 2-[1-(4-phenylphenoxy)ethyl]oxirane with an (R)- or (S)-configuration at the exocyclic stereocenter as central intermediates. These substances were obtained by separation of the non-stereoselectively synthesized epoxide into its racemic diastereomers by reversed phase chromatography followed by Jacobsen's hydrolytic kinetic resolution of each enantiomer with the (S)-configured oxirane ring. Furthermore, a chiral pool based enantioselective synthesis was developed. In that case, the starting compound for both target enantiomers was methyl 3, 4-O-isopropylidene-L-threonate. In comparison to the first approach, the chiral pool synthesis consisted of more steps, but generated the enantiomers with much better enantiomeric excess. Biological evaluation showed that the (R)-enantiomer inhibits isolated fatty acid amide hydrolase with a 200-fold higher activity than the (S)-enantiomer.

N- (6- ( (2R,3S) -3,4-DIHYDROXYBUTAN-2-YLOXY) -2- (4 - FLUOROBENZYLTHIO) PYRIMIDIN- 4 - YL) -3- METHYLAZETIDINE- 1 - SULFONAMIDE AS CHEMOKINE RECEPTOR MODULATOR

There is provided a compound which is (a) a pyrimidine sulfonamide of formula (I) or (b) a pharmaceutically acceptable salt thereof, crystalline forms of the compound, processes for obtaining the compound, pharmaceutical intermediates used in the manufacture of the compound, and pharmaceutical compositions containing the compound. The compound is useful in the treatment of a disease/condition in which modulation of chemokine receptor activity is beneficial.