39771-00-1

Upstream product

• 2930-05-4 Benzyloxymethyl-oxiran 
• 100-51-6 benzyl alcohol 

Downstream Products

• 867018-46-0 1-benzyloxy-3-N,N-dibenzylamino-2-propylmercaptan 
• 867018-52-8 1-benzyloxy-3-N,N-dibenzylaminopropane-2-sulfonic acid 
• 867018-39-1 1-amino-3-(benzyloxy)propane-2-sulfonic acid 

Relevant academic research and scientific papers

Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92% e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)4] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)2] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by 31P NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)2] gave the enantiomeric complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4.

Facile synthesis of thietanes via ring expansion of thiiranes

Thietanes are pharmaceutically important cores of some biological compounds and intermediates of organic synthesis. Various thietanes were prepared from thiiranes via ring expansion through a reaction with trimethyloxosulfonium iodide in the presence of sodium hydride. The reaction process is a nucleophilic ring-opening reaction of thiiranes with dimethyloxosulfonium methylide, generated from trimethyloxosulfonium iodide and sodium hydride, and subsequent intramolecular displacement (cyclization) of thiolates to the dimethyloxosulfonium moiety. The current method provides a new strategy for efficient preparation of thietanes from readily available thiiranes.

An improved method for the conversion of oxiranes to thiiranes and the discrimination of their base peaks in EI-MS

An efficient method for the conversion of oxiranes to thiiranes by treatment with excess ammonium thiocyanate in aqueous media under reflux or by microwave irradiation is reported. ARKAT-USA, Inc.

Synthesis of α-aliphatic and β-aromatic substituted taurines via regioselective ring opening of thiiranes with ammonia

Thiiranes are important starting materials for the synthesis of substituted taurines. The regioselectivity of ring-opening reactions of thiiranes with ammonia in the presence of silver nitrate was investigated. The results of the ring-opening reaction and subsequent peroxy acid oxidation indicate that alkyl-substituted thiiranes give rise to 1-monoalkyl- and 1,1-dialkyltaurines, whereas aryl-substituted thiiranes produce 2-aryl-, 2-alkyl-2-aryl-, and 2,2-diaryltaurines. This shows that alkyl-substituted thiiranes were attacked on their less-substituted ring carbon atoms, while aryl-substituted thiiranes were attacked on their more substituted ring carbon atoms. The current method is an effective and atom-economic route for the synthesis of mono- and disubstituted α-alkyl-and β-aryl-substituted taurines. Georg Thieme Verlag Stuttgart.

Iodine as a mild, efficient, and cost-effective catalyst for the synthesis of thiiranes from oxiranes

We developed an efficient protocol for the synthesis of thiiranes from oxiranes using a catalytic amount of molecular iodine. The notable features of this procedure are mild reaction conditions, high conversions, short reaction times, economic viability o

A new and efficient method for the synthesis of thiiranes from oxirane-β-cyclodextrin complexes and thiourea in water

Oxiranes react smoothly with thiourea in the presence of β-cyclodextrin in water at room temperature under neutral conditions to afford the corresponding thiiranes in excellent yields; the β-cyclodextrin can be recycled.

Indium tribromide: A novel and highly efficient reagent for the conversion of oxiranes to thiiranes

Epoxides react smoothly with potassium thiocyanate in the presence of 5 mol% of indium tribromide under mild and convenient reaction conditions to afford the corresponding thiiranes in high yields. This method is compatible with a wide range of protecting groups and functional groups such as alkenes, alkynes, esters, THP, TBDMS, and PMB ethers present in the molecule.