125356-51-6

Basic information

• Product Name: (1S,2S)-trans-2-azidocyclopentanol
• Synonyms: (1S,2S)-trans-2-azidocyclopentanol
• CAS NO: 125356-51-6
• Molecular Weight: 127.146
• Mol File: 125356-51-6.mol

Chemical Properties

• CAS DataBase Reference: (1S,2S)-trans-2-azidocyclopentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-trans-2-azidocyclopentanol(125356-51-6)
• EPA Substance Registry System: (1S,2S)-trans-2-azidocyclopentanol(125356-51-6)

Safety Data

• Hazardous Substances Data: 125356-51-6(Hazardous Substances Data)

Upstream product

• 88807-02-7 (±)-trans-2-azidocyclopentanol 
• 285-67-6 Cyclopentene oxide 
• 756874-86-9 (1S,2S)-2-azido-cyclopentyl butyrate 
• 108-05-4 vinyl acetate 

Downstream Products

• 168749-07-3 (1R,2S)-cis-2-azidocyclopentanol 
• 1435876-19-9 (1R,2S)-cis-2-(4-phenoxybenzenesulfonamido)cyclopentanol 
• 1449419-07-1 (1S,2S)-trans-2-(4-phenoxybenzenesulfonamido)cyclopentyl thiobenzoate 
• 1435876-35-9 (1S,2S)-(+)-trans-2-(4-phenoxybenzenesulfonamido)cyclopentanethiol 
• 145106-43-0 (1S,2S)-trans-2-(tert-butoxycarbonylamino)cyclopentanol 
• 445479-01-6 (1R,2S)-2-tert-Butoxycarbonylaminocyclopentylamine 
• 930-45-0 (1S,2S)-2-aminocyclopentanol 

Relevant articles and documents

Matrix metalloproteinase inhibitors based on the 3-mercaptopyrrolidine core

New series of pyrrolidine mercaptosulfide, 2-mercaptocyclopentane arylsulfonamide, and 3-mercapto-4-arylsulfonamidopyrrolidine matrix metalloproteinase inhibitors (MMPIs) were designed, synthesized, and evaluated. Exhibiting unique properties over other MMPIs (e.g., hydroxamates), these newly reported compounds are capable of modulating activities of several MMPs in the low nanomolar range, including MMP-2 (～2 to 50 nM), MMP-13 (～2 to 50 nM), and MMP-14 (～4 to 60 nM). Additionally these compounds are selective to intermediate- and deep-pocket MMPs but not shallow-pocketed MMPs (e.g., MMP-1, ～850 to >50 000 nM; MMP-7, ～4000 to >25 000 nM). Our previous work with the mercaptosulfide functionality attached to both cyclopentane and pyrrolidine frameworks demonstrated that the cis-(3S,4R)-stereochemistry was optimal for all of the MMPs tested. However, in our newest compounds an interesting shift of preference to the trans form of the mercaptosulfonamides was observed with increased oxidative stability and biological compatibility. We also report several kinetic and biological characteristics showing that these compounds may be used to probe the mechanistic activities of MMPs in disease.

Enantioselective ring-opening of aziridines

A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst

(1S,2R/1R,2S)-cis-cyclopentyl PNAs (cpPNAs) as constrained PNA analogues: Synthesis and evaluation of aeg-cpPNA chimera and stereopreferences in hybridization with DNA/RNA

Conformationally constrained chiral PNA analogues were designed on the basis of stereospecific imposition of a 1,2-cis-cyclopentyl moiety on an aminoethyl segment of aegPNA. It is known that the cyclopentane ring is a relatively flexible system in which the characteristic puckering dictates the pseudoaxial/pseudoequatorial dispositions of substituents. Hence, favorable torsional adjustments are possible to attain the necessary hybridization- competent conformations when the moiety is imposed on the conventional PNA backbone. The synthesis of the enantiomerically pure 1,2-cis-cyclopentyl PNA monomers (10a and 10b) was achieved by stereoselective enzymatic hydrolysis of a key intermediate ester 2. The chiral (1S,2R/1R,2S)-aminocyclopentylglycyl thymine monomers were incorporated into PNA oligomers at defined positions and through the entire sequence. Hybridization studies with complementary DNA and RNA sequences using UV-Tm measurements indicate that aeg-cpPNA. chimera form thermally more stable complexes than aegPNA with stereochemistry-dependent selective binding of cDNA/RNA. Differential gel shift retardation was observed on hybridization of aeg-cpPNAs with complementary DNA.

Synthesis and evaluation of new 1,7-dioxaspiro[5.5]undecane ligands: Implications for the use of diols in the desymmetrization of meso epoxides

The synthesis and preliminary evaluation of two new chiral 1,7- dioxaspiro[5.5]undecane ligands is described. The compounds of interest are readily available in enantiomerically pure form. Chiral organotitanium complexes prepared from these ligands cataly

Cr(salen) catalysed asymmetric ring opening reactions of epoxides in room temperature ionic liquids

Cr(salen) catalysed asymmetric ring opening reactions of epoxides with TMSN3 proceed readily in the room temperature ionic liquid 1-butyl-3-methylimidazolium salts ([bmim][X]) with easy catalyst/solvent recycling.

Lipase-catalyzed Kinetic Resolution of (+/-)-trans- and cis-2-Azidocycloalkanols

The lipase-catalyzed kinetic resolution of trans- and cis-2-azidocycloalkanols and the preparation of enantiomerically pure trans- and cis-2-aminocycloalkanols are described. Four kinds of lipases were screened for the acetylation of trans- and cis-2-azidocycloalkanols. Among them, Pseudomonas sp. lipases (lipase PS and lipase AK, Amamo Pharmaceutical Co.) showed the highest enantioselectivity. These products were converted to the corresponding 2-aminocycloalkanols to determine their enantiomeric excess (ee) and absolute configurations by HPLC and CD analyses, using (S)-TBMB carboxylic acid [(S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid] as the chiral conversion reagent. The results of the CD analysis proved N,O-bis-(S)-TBMB carboxylated cis-2-aminocycloalkanols to adopt a predominantly N-equatorial conformation. The partially resolved trans- and cis-2-aminocycloalkanols, except for trans-2-aminocyclopentanol, were recrystallized from ethyl acetate to give enantiomerically pure forms.