(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Name: (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
Brand: ChemScene
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CAS No. 361440-67-7
Cat. No. CS-0030786
Purity≥97%
MDL No.MFCD13151933

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(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester|CS-0030786

Structure of 361440-67-7

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Description

This tert-butyl ester derivative features a rigid, stereochemically defined bicyclic scaffold with a pendant aminocarbonyl group. The (1S,3S,5S) configuration ensures precise spatial orientation for targeted interactions in synthetic and medicinal chemistry applications. Bench-stable and moisture-tolerant, it serves as a key building block for constrained peptidomimetics and bioactive heterocycles.

Application

(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester serves as a conformationally constrained building block for medicinal chemistry campaigns targeting GPCR modulators and kinase inhibitors. Its rigid bicyclic core enables precise spatial orientation of the amide and ester functionalities, facilitating selective coupling reactions and improving metabolic stability in lead optimization. The tert-butyl ester group offers excellent bench stability and simplifies purification via standard acid-labile deprotection protocols.

General Information

CAS No. 361440-67-7
Cat. No. CS-0030786
Purity ≥97%
MDL No. MFCD13151933
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₈N₂O₃
Molecular Weight 226.27
Synonym(s) Saxagliptin Intermediate
SMILES O=C(OC(C)(C)C)N1[C@]2(C[C@]2(C[C@H]1C(N)=O)[H])[H]

Computational Chemistry Data

TPSA 72.63
LogP 0.8696
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

CAS No. 361440-67-7

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