(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

CAS No. 197142-34-0
Cat. No. CS-W018696
Molecule weight227.26
Purity≥97%
MDL No.MFCD08691405

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(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid|CS-W018696

Structure of 197142-34-0

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General Information

CAS No. 197142-34-0
Cat. No. CS-W018696
Purity ≥97%
MDL No. MFCD08691405
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₇NO₄
Molecular Weight 227.26
Synonym(s) N-tert-butoxycarbonyl-l-trans-2-azabicyclo 3.1.0 hexane-3-carboxylic acid
SMILES O=C([C@H]1N(C(OC(C)(C)C)=O)[C@]2([H])C[C@]2([H])C1)O

Description

This bicyclic scaffold features a stereochemically defined azabicyclo[3.1.0]hexane core bearing a tert-butoxycarbonyl-protected amine and a carboxylic acid at the 3-position, enabling direct incorporation into complex molecular architectures via standard coupling protocols. The rigid framework imparts conformational control, while the orthogonal functional groups allow selective derivatization in synthetic sequences.

Application

(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid serves as a conformationally constrained building block for medicinal chemistry, enabling the synthesis of bioactive heterocycles through established coupling and functionalization protocols. Its tert-butyl carbamate group provides excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. The bicyclic scaffold exhibits defined stereochemistry and functional group tolerance, making it well-suited for modular peptide-like and small-molecule library construction.

Synthesis

Route1
- 197142-33-9
- ~75%
- In-stock
  
  197142-34-0
References
- Hanessian, Stephen; Reinhold, Ulrich; Gentile, Gabriella Angewandte Chemie (International Edition in English), 1997 , vol. 36, # 17 p. 1881 - 1884
Route2
- In-stock
  
  24424-99-5
- 1312338-82-1
- ~76%
- In-stock
  
  197142-34-0
References
- BRISTOL-MYERS SQUIBB COMPANY; PACK, Shawn, K.; TYMONKO, Steven; PATEL, Bharat, P.; NATALIE, JR., Kenneth, J.; BELEMA, Makonen Patent: WO2011/59850 A1, 2011 ; Location in patent: Page/Page column 179-180 ;
Route3
- 1208008-34-7
- ~60%
- In-stock
  
  197142-34-0
References
- BRISTOL-MYERS SQUIBB COMPANY; PACK, Shawn, K.; TYMONKO, Steven; PATEL, Bharat, P.; NATALIE, JR., Kenneth, J.; BELEMA, Makonen Patent: WO2011/59850 A1, 2011 ; Location in patent: Page/Page column 178-179 ;

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 66.84
LogP 1.4689
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

CAS No. 197142-34-0

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