(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Name: (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 23680-31-1
Cat. No. CS-W004063
Purity≥96%
MDL No.MFCD00066063

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid|CS-W004063

Structure of 23680-31-1

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General Information

CAS No. 23680-31-1
Cat. No. CS-W004063
Purity ≥96%
MDL No. MFCD00066063
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₁NO₅
Molecular Weight 295.33
Synonym(s) None
SMILES O=C(O)[C@H](COCC1=CC=CC=C1)NC(OC(C)(C)C)=O

Description

(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid is a chiral building block featuring a protected amino group and a labile benzyloxy handle. This combination enables selective deprotection and functionalization under mild conditions, streamlining access to advanced peptide analogs and bioactive scaffolds in synthetic medicinal chemistry workflows.

Application

(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid serves as a valuable chiral building block for peptide synthesis and medicinal chemistry. The Boc-protected amine enables straightforward deprotection and coupling, while the benzyloxy group offers orthogonal stability and convenient removal via hydrogenolysis. Its bench-stable nature and compatibility with standard peptide coupling protocols facilitate efficient access to complex scaffolds.

Synthesis

Route1
- In-stock
  
  3262-72-4
- 100-39-0
- ~99%
- In-stock
  
  23680-31-1
References
- Gravestock, David; Rousseau, Amanda L.; Lourens, Anna C.U.; Hoppe, Heinrich C.; Nkabinde, Lindiwe A.; Bode, Moira L. Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3225 - 3229
Route2
- 69871-79-0
- ~96%
- In-stock
  
  23680-31-1
References
- Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 1998 , vol. 54, # 46 p. 13981 - 13996
Route3
- In-stock
  
  24424-99-5
- In-stock
  
  4726-96-9
- ~93%
- In-stock
  
  23680-31-1
References
- Ramasamy, Kanda S.; Stoisavljevic, Vesna Nucleosides and Nucleotides, 1999 , vol. 18, # 8 p. 1845 - 1861

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 84.86
LogP 2.1811
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Serine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

CAS No. 23680-31-1

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