3206-47-1

Usage

Structure

Tetrazole ring with a 1-phenyl-5-[(1-methylethyl)thio] substitution

Family

Tetrazole compounds

Use as pharmaceutical intermediate

Synthesizes various drugs

Investigated properties

Biological and pharmacological

Building block

Synthesis of other organic compounds

Precaution

Potential hazards, handle with care

Safety guidelines

Consult safety data sheets and guidelines before use

Upstream product

• 14210-25-4 5-Chloro-1-phenyltetrazole 
• 75-26-3 isopropyl bromide 
• 99418-52-7 isopropyl 2,2,2-trichloroacetimidate 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 67-63-0 isopropyl alcohol 
• 86-93-1 1-phenyl-1H-tetrazole-5-thiol 

Downstream Products

• 3043-64-9 1-phenyl-5-(propane-2-sulfonyl)-pr1H-tetrazole 

Relevant academic research and scientific papers

Total Synthesis of the Marine Macrolide Amphidinolide F

A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.

Alkylation of thiols with trichloroacetimidates under neutral conditions

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

A diels-alder approach to (-)-ovalicin

A round at the Oval: The antiangiogenic activity of the natural product ovalicin has sparked significant interest. A highly efficient enantio- and diastereoselective total synthesis of ovalicin proved successful in which the key step involved an endo sele

Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies

The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the Mgl 2-mediated ring-expansion reaction of a spiro[cyclopropane-1, 3′-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocienski olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.

Tetrazoles. XXXI. Phase-Transfer Reactions of 1-Substituted Tetrazole-5-thiones and Their Derivatives

Alkylation of 1-substituted tetrazole-5-thiones under conditions of phase-transfer catalysis in the two-phase system liquid-liquid proceeds regioselectively at the sulfur atom, regardless of the alkylating agent and phase-transfer catalyst. Phase-transfer oxidation of the 5-alkylthiotetrazoles thus obtained by potassium permanganate is a convenient method for preparation of 5-alkylsulfonyltetrazoles which can be used to synthesize functionally substituted tetrazoles.