130981-12-3

Usage

Uses

Used in Pharmaceutical Research:
(1R,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure, including the cyclopentane ring and Boc-amino protective group, allows for the development of new drug candidates with potential therapeutic applications.
Used in Material Science:
(1R,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid is used as a building block in the creation of novel materials with specific properties. The presence of the carboxylic acid group enables the formation of esters, amides, and other functional groups, which can be exploited to design materials with tailored characteristics for various applications in material science.
Used in Organic Synthesis:
(1R,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid is used as a reagent in organic synthesis, particularly for the preparation of amines and other nitrogen-containing compounds. The Boc-amino group serves as a protective agent, allowing for selective reactions and facilitating the synthesis of complex molecules with controlled functional group manipulation.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(15)12-8-6-4-5-7(8)9(13)14/h7-8H,4-6H2,1-3H3,(H,12,15)(H,13,14)/t7-,8+/m1/s1

Upstream product

• 136315-70-3 (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid 
• 110-87-2 3,4-dihydro-2H-pyran 
• 57795-10-5 5-(1',3'-dithian-2'-yl)-1-pentanol 
• 57043-00-2 (1RS,2SR)-cispentacin 
• 145213-19-0 (R)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-ol 
• 145150-93-2 (+/-)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-ol 
• 145150-86-3 (R)-(E)-7-hydroxy-5-octenal 
• 145213-17-8 (+/-)-(E)-7-(1,3-dithian-2-yl)-3-hepten-2-yl acetate 
• 152495-66-4 (E)-7-(1,3-dithian-2-yl)-3-hepten-2-one 
• 145150-91-0 2-(3-formylpropyl)-1,3-dithiane 
• 111741-88-9 5-(1',3'-dithian-2'-yl)-1-(2-tetrahydropyranyloxy)pentane 
• 623582-45-6 (R)-2-(3aR,6aS)-Hexahydro-cyclopenta[c]isoxazol-1-yl-2-phenyl-ethanol 
• 228422-38-6 (1S,2R)-1-amino-2-(hydroxymethyl)cyclopentane 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 122672-46-2 (-)-cispentacin 
• 494209-39-1 C₆H₁₂N₂O*(x)ClH 
• 76-05-1 trifluoroacetic acid 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors

The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described.

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

The proposed diastereoisomers (1 a–d) together with their C8′-epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.

Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.

Synthesis of racemic and optically active cispentacin (FR109615) using intramolecular nitrone-olefin cycloaddition

Synthesis of racemic and optically active cispentacin ((-)-1) is described. Intramolecular nitrone-olefin cycloaddition of the alkenyl nitrone 7 gave cis-isoxazolidine (±)-8, which was transformed into (±)-1 by sequential reactions involving catalytic hyd