50896-54-3

Usage

Chemical Properties

Colorless to light yellow liqui

InChI:InChI=1/C11H16O3S/c1-4-10(3)14-15(12,13)11-7-5-9(2)6-8-11/h5-8,10H,4H2,1-3H3/t10-/m0/s1

Upstream product

• 4221-99-2 (S)-2-butanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 408351-96-2 di(8-hydroxy-1-naphthyl)disulfide 
• 62972-63-8 2-methyl-2H-naphtho[1,8-cd]isothiazole 1,1-dioxide 

Downstream Products

• 3306-36-3 (1R)-1-methylpropyl benzoate 
• 131432-56-9 (R)-sec-butyl p-tolyl sulfide 
• 29707-98-0 (R)-(-)-s-butyl phenyl ether 
• 149809-44-9 (R)-2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 152141-79-2 (R)-(-)-s-butyl phenyl sulfide 
• 87106-27-2 (R)-2-methyl-1-phenylsulfonylbutane 
• 1432745-74-8 1,4-dibromo-2,5-di((R)-sec-butoxy)benzene 
• 27826-44-4 (R)-(-)-s-butyl p-nitrophenyl sulfide 
• 264906-20-9 ethyl-3-[(R)-sec-butoxy]benzoate 

Relevant academic research and scientific papers

Emergent Self-Assembly Pathways to Multidimensional Hierarchical Assemblies using a Hetero-Seeding Approach

The controlled formation of complex and functional 1-, 2-, and 3D hierarchical assemblies from molecular building blocks represents a key current challenge. Herein, we report the use of a seeded growth approach for a series of perylenediimide-based molecules (PDIs 1–4) to access otherwise inaccessible self-assembly pathways that yield complex hierarchical structures. The key to the new approach is to use hetero-seeds which possess a different composition and morphology from that of the molecular building block. For example, a nanotube seed (from PDI 3) and a microribbon seed (from PDI 4) were found to initiate different self-assembly pathways for PDI 1, which normally assembles to yield nanocoils. This led to the formation of unprecedented 3D scroll-like and scarf-like hierarchical nanostructures, respectively. Also, the hetero-seeds from PDI 3 initiate hidden self-assembly pathways of PDI 2 to generate 1D tubular heterojunctions. Significantly, this new strategy offers new opportunities to create emergent and functional hierarchical and complex structures from small molecule precursors.

Kinetic Control of a Self-Assembly Pathway towards Hidden Chiral Microcoils

Manipulating the self-assembly pathway is essentially important in the supramolecular synthesis of organic nano- and microarchitectures. Herein, we design a series of photoisomerizable chiral molecules, and realize precise control over pathway complexity with external light stimuli. The hidden single-handed microcoils, rather than the straight microribbons through spontaneous assembly, are obtained through a kinetically controlled pathway. The competition between molecular interactions in metastable photostationary intermediates gives rise to a variety of molecular packing and thereby the possibility of chirality transfer from molecules to supramolecular assemblies.

New method for synthesis of EZH2 methyltransferase inhibitor GSK126

GSK126 is a potent small-molecule inhibitor of S-adenosyl-methionine-competitive EZH2 methyltransferase and has the potential to be used clinically for preventing unwanted histone methylation of tumor suppressor genes. In this article, we describe a new s

Highly fluorescent one-handed nanotubes assembled from a chiral asymmetric perylene diimide

Highly fluorescent bilayer nanotubes with a right- or left-handed helical sense were assembled from a chiral asymmetric perylene diimide for the first time, which constitute a new family member of self-assembled organic nanotubes.

Synthesis of optically active regioregular polythiophenes and their self-organization at the air-water interface

Regioregular polythiophenes containing an optically active substituent in the third position of the thiophene ring, head-to-tail poly(3-[2-((S)-1- methyloctyloxy)ethyl]thiophene)s (HT-P(S)MOETs), were synthesized using highly reactive zinc. For comparison

Molecular tectonics: Homochiral 3D cuboid coordination networks based on enantiomerically pure organic tectons and ZnSiF6

Upon combining enantiomerically pure bis-monodentate organic tectons with ZnSiF6, homochiral 3D cuboid architectures displaying chiral channels are formed.

Synthesis of four stereoisomers of (S)-2-methylpent-3-yl 3,13-dimethylpentadecanoate, a sex pheromone of the bagworm moth clania variegate, using stereospecific inversion of secondary sulfonates as a key step

Females of some lepidopteran species produce novel sex pheromones with a methyl-branched structure, such as 2-methylpent-3-yl 3,13-dimethylpentadecanoate secreted by the bagworm moth Clania variegate. Recently, we have established a simple preparative method for the synthesis of methyl-branched building blocks by utilizing an SN2 reaction of chiral secondary tosylates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by their application in the synthesis of all four stereoisomers of an acid moiety in the bagworm pheromone. The enantiomeric purities of all building blocks were confirmed by enantioselective HPLC analysis. We found that a secondary mesylate was superior to the corresponding tosylate because it avoided an elimination side reaction, and racemization in the SN2 reaction was not observed even at high temperature (150 °C). Finally, each optically active acid was esterified with (S)-2-methyl-3-pentanol, which was synthesized by a new route starting from (S)-valine. A simple route to methyl-branched building blocks has been developed by utilizing an S N2 reaction of chiral secondary sulfonates derived from (S)- and (R)-propylene oxides. The usefulness of these building blocks was demonstrated by the stereospecific synthesis of all four stereoisomers of a bagworm pheromone. Copyright

Impact of absolute stereochemistry on the antiangiogenic and antifungal activities of itraconazole

Itraconazole is used clinically as an antifungal agent and has recently been shown to possess antiangiogenic acitivity. Itraconazole has three chiral centers that give rise to eight stereoisomers. The complete role of stereochemistry in the two activities of itraconazole, however, has not been addressed adequately. For the first time, all eight stereoisomers of itraconazole (1a?h) have been synthesized and evaluated for activity against human endothelial cell proliferation and for antifungal activity against five fungal strains. Distinct antiangiogenic and antifungal activity profiles of the trans stereoisomers, especially 1e and 1f, suggest different molecular mechanisms underlying the antiangiogenic and antifungal activities of itraconazole.

Itraconazole and saperconazole stereoisomers

The present invention is concerned with the stereoisomeric forms of itraconazole (X=Cl) and saperconazole (X=F), which may be represented by the formula and the pharmaceutically acceptable acid addition salt forms thereof, processes for preparing said stereoisomeric forms, the complexes thereof with cyclodextrin derivatives, pharmaceutical compositions comprising said complexes and methods of preparing said complexes and pharmaceutical compositions.

Synthesis and structure of poly(phenyl isocyanate)s bearing an optically active alkoxyl group

Novel optically active phenyl isocyanate derivatives (1-6) bearing an (R)-sec-butoxy, (S)-2-methylbutoxy or (S)-3,7-dimethyloctyloxy group at the meta or para position on the phenyl ring were prepared and polymerized with an anionic initiator in tetrahydrofuran (THF). The resulting polymers from 1, 2, 4 and 6 showed much greater specific rotation than that of the corresponding monomers and an intense circular dichroism (CD) band in the main-chain absorption region, indicating that these polymers have a predominantly one-handed helical conformation in solution. On the other hand, the polymers obtained from 3 and 5 showed a much smaller specific rotation than that of the above polymers at room temperature. The polymers from 2 and 5 showed a remarkable change in optical activity with change in temperature, and the specific rotation of the polymers changed from a positive to a negative value with decrease in temperature. The CD band of the polymers in the absorption region due to the main chain changed from a positive to a negative peak with a change in specific rotation. These results indicate that poly-2 and poly-5 undergo a thermally induced helix-helix transition in THF. The temperature for the helix-helix transition of poly-2 was independent of the degree of polymerization. Poly-2 exhibited a reversible helix-helix transition in chloroform and diethyl ether and also in THF, whereas in toluene and dichloromethane such a transition was not observed. Copyright