(1R,2S,5S)-6,6-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Name: (1R,2S,5S)-6,6-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
Brand: ChemScene
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CAS No. 219754-02-6
Cat. No. CS-0060909
Purity≥97%
MDL No.MFCD15147269

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(1R,2S,5S)-6,6-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid|CS-0060909

Structure of 219754-02-6

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Description

This bicyclic carbamate scaffold features a sterically hindered tert-butyl ester and a chiral framework with defined stereochemistry at the 1R,2S,5S positions. The dimethyl substitution enhances lipophilicity and metabolic stability, while the protected carboxylic acid enables modular derivatization under standard conditions. This structural motif serves as a rigid, conformationally constrained building block for peptidomimetic and medicinal chemistry applications.

Application

(1R,2S,5S)-6,6-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid serves as a rigid, conformationally constrained bicyclic scaffold with defined stereochemistry, enabling precise spatial presentation of functional groups in medicinal chemistry campaigns. The tert-butyl carbamate (Boc) group provides robust protection for the secondary amine, facilitating selective deprotection and downstream derivatization. Its bench-stable nature and compatibility with standard coupling protocols make it ideal for building complex heterocyclic motifs and peptidomimetics.

General Information

CAS No. 219754-02-6
Cat. No. CS-0060909
Purity ≥97%
MDL No. MFCD15147269
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₁NO₄
Molecular Weight 255.31
Synonym(s) (1R,2S,5S)-3-(Tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
SMILES CC(C)(OC(N1C[C@@]2([H])[C@@](C2(C)C)([H])[C@H]1C(O)=O)=O)C

Computational Chemistry Data

TPSA 66.84
LogP 1.9625
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-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(1R,2S,5S)-6,6-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

CAS No. 219754-02-6

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