5-[(tert-Butoxycarbonyl)amino]bicyclo[3.1.1]heptane-1-carboxylic Acid TCI B6607

Chemical Identity

Other names: 5-(Boc-amino)bicyclo[3.1.1]heptane-1-carboxylic Acid
CAS No.: 1035325-28-0
PubChem: CID 25324809
Formula: C13H21NO4
Molecular weight: 255.31 g/mol
Purity: >98.0%(GC)(qNMR)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 5-[(2-methylpropan-2-yl)oxycarbonylamino]bicyclo[3.1.1]heptane-1-carboxylic acid
SMILES: CC(C)(C)OC(=O)NC12CCCC(C1)(C2)C(=O)O
InChIKey: VJMSCDJQBXPPAR-UHFFFAOYSA-N
MDL: MDL13806407

Rp 6.916.350,00

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Berat 100mg

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TCI B6607 is 5-[(tert-butoxycarbonyl)amino]bicyclo[3.1.1]heptane-1-carboxylic acid, a rigid saturated building block with orthogonal carboxylic acid and Boc-protected amine handles. The bicyclo[3.1.1]heptane core is widely investigated as a three-dimensional bioisostere for meta-substituted benzene rings. Replacing flat aromatic rings with such saturated cages can improve solubility and reduce metabolic liability in lead optimisation programmes. AMI Scientific supplies this TCI building block in a 100 mg pack size for synthetic and medicinal chemistry laboratories.

TCI brochures (PDF)

Bicycloalkane Building Blocks ― Benzene Bioisosteres ― 2025-04-01 · p. 1

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Baenziger et al. (2015). ChemInform Abstract: Development Approaches Towards a 4‐Spiro Cyclopropane Proline Scaffold (S)‐5‐(tert‐Butoxycarbonyl)‐5‐azaspiro[2.4]heptane‐6‐carboxylic Acid. ChemInform doi:10.1002/chin.201536288
Kadyrov et al. (2021). Convenient Synthesis of (R)-3-[(tert-Butoxycarbonyl)amino]piperidine and (R)-3-[(tert-Butoxycarbonyl)amino]azepane. Synthesis doi:10.1055/a-1526-7657
Matković (2024). 4-(2-(5-(2-(tert-Butoxycarbonyl)hydrazinecarbonyl)-2-methylthiophen-3-yl)cyclopent-1-enyl)-5-methylthiophene-2-carboxylic Acid. Molbank doi:10.3390/m1760

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.

References cited in the TCI brochure

Pavel K. Mykhailiuk. Saturated bioisosteres of benzene: where to go next? Organic & Biomolecular Chemistry, 2019. doi:10.1039/c8ob02812e
Toranosuke Iida. Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes Journal of the American Chemical Society, 2022. doi:10.1021/jacs.2c09733