5449-08-1

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-2-sulfanylcyclopentanol is utilized as a building block in organic synthesis for the preparation of pharmaceuticals and fine chemicals. Its presence of a sulfur atom and chiral nature make it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R,2R)-2-sulfanylcyclopentanol is used as an intermediate in the synthesis of various drugs. Its unique reactivity and chirality contribute to the development of new and effective medications.
Used in Asymmetric Synthesis:
(1R,2R)-2-sulfanylcyclopentanol is employed as a chiral auxiliary in asymmetric synthesis, which is crucial for producing enantiomerically pure compounds. This application is vital for the creation of biologically active molecules with specific pharmacological properties.
Used in Catalysis:
(1R,2R)-2-sulfanylcyclopentanol also finds use in catalysis, where its chiral properties can be harnessed to create enantioselective catalysts. This allows for the production of enantiomerically enriched products, which is essential in the synthesis of chiral molecules with desired biological activities.
Overall, (1R,2R)-2-sulfanylcyclopentanol is a versatile and valuable compound in the field of organic chemistry, with applications spanning across various industries and research areas.

Upstream product

• 285-67-6 Cyclopentene oxide 
• 285-67-6 (1S,5R)-6-Oxa-bicyclo[3.1.0]hexane 
• 108323-06-4 (+/-)-cis-1-acetoxy-2-acetylsulfanyl-cyclopentane 
• 933-06-2 1-acetoxycyclopentene 
• 2126-13-8 (+/-)-cis-tetrahydro-cyclopent[1,3]oxathiol-2-one 
• 124-41-4 sodium methylate 
• 142-29-0 cyclopentene 
• 93604-41-2 (+/-)-thiobenzoic acid S-(trans-2-hydroxy-cyclopentyl ester) 

Downstream Products

• 100061-29-8 (+/-)-trans-2-(2,4-dinitro-phenylsulfanyl)-cyclopentanol 

Relevant academic research and scientific papers

PEPTIDE CONJUGATES OF CYTOTOXINS AS THERAPEUTICS

The present invention relates to peptide conjugates of cytotoxins such as topoisomerase I inhibitors which are useful for the treatment of diseases such as cancer.

Catalytic asymmetric synthesis of thiols

The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected β-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.

A practical synthesis of differentially-protected cis-1,2-cyclopentanedithiols and cis-3,4-pyrrolidinedithiols

A practical method for the synthesis of cis-1,2-cyclopentanedithiols and cis-3,4-pyrrolidinedithiols with differentially protected sulfurs, needed for the design of new metal-chelating ligands, has been developed.

Studies on the Reaction of Mitomycin C with Potassium Ethyl Monothiocarbonate under Reductive Conditions

Treatment of mitomycin C (1) with the ambident nucleophile potassium ethyl monothiocarbonate (2) under reductive conditions (sodium dithionite) at approximately neutral pH at room temperature led to the formation of equivalent amounts of trans- (17) and cis- (18) aziridine ring-opened disubstituted mitosene adducts.In both cases substitution at carbons 1 and 10 proceeded with sulfur attack.The structural identity of each product was confirmed by high-field 1H and 13C NMR spectral ananlysis as well as by chemical studies.Milder conditions (0-5 deg C) led to the isolation of both trans- (22) and cis- (23) aziridine ring-opened monosubstituted adducts.Compounds 22 and 23 were converted to the corresponding disubstituted products by treatment with additional 2 and sodium dithionite.The implications of these reactions in relation to the mode of action of mitomycin C (1) are discussed.