40348-74-1

Upstream product

• 96-09-3 styrene oxide 
• 104-15-4 toluene-4-sulfonic acid 
• 93-56-1 phenylethane 1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 

Downstream Products

• 127840-18-0 Acetic acid (S)-1-phenyl-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 945985-19-3 C₂₁H₃₀O₄SSi 
• 124718-87-2 2-azido-1-phenylethan-1-ol 
• 1258048-39-3 C₂₀H₂₂O₆S 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 488785-29-1 (2S*,6R*)-2,6-diphenyl-4-tosylmorpholine 
• 4427-92-3 4-Phenyl-1,3-dioxolan-2-one 
• 96-09-3 styrene oxide 
• 945985-20-6 C₂₁H₂₆O₅ 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 

Relevant academic research and scientific papers

Selective sulfonylation of 1,2-diols and derivatives catalyzed by a recoverable fluorous tin oxide

Fluorous tin oxide (C6F13CH2CH2)2SnO is readily synthesized, exhibits spectra that are generally similar to dibutyltin oxide and appears to exist as an oligomer or polymer. The fluorous tin oxide can be used catalytically to effect the selective monotosylation of 1,2-diols with TsCl/Et3N, and it can be readily recovered and reused. (C) 2000 Published by Elsevier Science Ltd.

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

9-Hetero-10-boraanthracene-derived borinic acid catalysts for regioselective activation of polyols

Heteraborinine-derived borinic acids serve as efficient catalysts for regioselective monofunctionalization of di- and polyols. Arylborinic acids of this type, wherein the B-OH group is incorporated into a 6π electron system, display both improved catalytic activity for functionalization of diols and enhanced stability towards air oxidation relative to the 'parent' diphenylborinic acid (Ph2BOH). These properties enable their applications at loadings as low as 0.1 mol% and without the need for a stabilizing precatalyst ligand (e.g., ethanolamine). Complexation studies, computation and kinetic data suggest that while the heteraborinine-derived borinic acids show significantly lower association constants with substrates than Ph2BOH, this effect is more than compensated for by the increased nucleophilicity of their tetracoordinate diol adducts.

Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: Expansion of substrate scope and mechanistic studies

Synthetic and mechanistic aspects of the diarylborinic acid-catalyzed regioselective monofunctionalization of 1,2- and 1,3-diols are presented. Diarylborinic acid catalysis is shown to be an efficient and general method for monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups (7 examples, 88% average yield). In addition, the scope of the selective acylation, sulfonylation, and alkylation is extended to 1,2- and 1,3-diols not derived from carbohydrates (28 examples); the efficiency, generality, and operational simplicity of this method are competitive with those of state-of-the-art protocols including the broadly applied organotin-catalyzed or -mediated reactions. Mechanistic details of the organoboron-catalyzed processes are explored using competition experiments, kinetics, and catalyst structure-activity relationships. These experiments are consistent with a mechanism in which a tetracoordinate borinate complex reacts with the electrophilic species in the turnover-limiting step of the catalytic cycle.

Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans

A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs.

Further improvements of the dibutyl tin oxide-catalyzed regioselective diol tosylation

In this Letter, we report that selective monotosylation of a 1,2-diol is possible using only 0.1 mol % of Bu2SnO. More interestingly, we found that the corresponding tin acetal 3b gave faster conversions and more reproducible reaction times. Moreover, the loading of this catalyst could be as low as 0.05-0.005 mol %.

Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition 'click-chemistry' in water

The synthesis of a new class of hybrid 1,2,3-triazozlo-δ-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition 'click-chemistry' reaction of various organic azides with an activated alkyne in water, followed by cyclization.

Substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes as β3-adrenergic receptor agonists: Design, synthesis, biological evaluation and pharmacophore modeling

In search of potent β3-adrenergic receptor agonists, a series of novel substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes has been synthesized and evaluated for their β3-adrenergic receptor agonistic activity (ranging from -17.73% to 90.64% inhibition at 10 μM) using well established Human SK-N-MC neuroblastoma cells model. Four molecules viz. 11, 15, 22 and 23 showed β3-AR agonistic IC50 value of 0.55, 0.59, 1.18 and 1.76 μM, respectively. These four candidates have been identified as possible leads for further development of β3-adrenergic receptor agonists for obesity and Type-II diabetes pharmacotherapy. The free OH and NH functions are found to be essential for β3-adrenergic receptor agonistic activity. Among the synthesized β3-adrenergic receptor agonists having 1,2,3,4-tetrahydroquinoline scaffold, the N-benzyl group is found to be superior over N-arylsulfonyl group. A putative pharmacophore model has been modeled considering the above four active molecules which distinguishes well between the active and inactive molecules.

Design, synthesis, and structure-activity relationship of carbamate-tethered aryl propanoic acids as novel PPARα/γ dual agonists

We have developed a new class of PPARα/γ dual agonists, which show excellent agonistic activity in PPARα/γ transactivation assay. In particular, (R)-9d was identified as a potent PPARα/γ dual agonist with EC50s of 0.377 μM in PPARα and 0.136 μM in PPARγ, respectively. Interestingly, the structure-activity relationship revealed that the stereochemistry of the identified PPARα/γ dual agonists significantly affects their agonistic activities in PPARα than in PPARγ.

Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight

This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.