(1R,4S,5S)-rel-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid

Name: (1R,4S,5S)-rel-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid
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CAS No. 615575-74-1
Cat. No. CS-0053602
Purity≥98%
MDL No.MFCD12198745

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(1R,4S,5S)-rel-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid|CS-0053602

Structure of 615575-74-1

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General Information

CAS No. 615575-74-1
Cat. No. CS-0053602
Purity ≥98%
MDL No. MFCD12198745
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₇NO₄
Molecular Weight 227.26
Synonym(s) 2-(Tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid
SMILES O=C(O)[C@H]1[C@H]2CN(C(OC(C)(C)C)=O)[C@@H]1C2

Description

This bicyclic scaffold features a stereochemically defined azabicyclo[2.1.1]hexane core with a tert-butoxycarbonyl-protected amine and a carboxylic acid at the 5-position, enabling direct incorporation into peptidomimetics and constrained bioactive molecules under standard coupling conditions.

Application

This bicyclic scaffold serves as a conformationally constrained building block for medicinal chemistry, enabling the synthesis of stereodefined heterocycles and peptidomimetics. The protected amine and carboxylic acid functionalities offer orthogonal reactivity, facilitating diverse coupling and functionalization reactions. Bench-stable and compatible with standard synthetic workflows, it functions as a key intermediate in the construction of bioactive molecules requiring rigid, three-dimensional architectures.

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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 66.84
LogP 1.3264
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Key Words

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(1R,4S,5S)-rel-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-5-carboxylic acid

CAS No. 615575-74-1

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