(2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid

Name: (2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid
Brand: ChemScene
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CAS No. 59969-65-2
Cat. No. CS-0162361
Molecule weight329.35
Purity≥98%
MDL No.MFCD23701663

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(2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid|CS-0162361

Structure of 59969-65-2

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General Information

CAS No. 59969-65-2
Cat. No. CS-0162361
Purity ≥98%
MDL No. MFCD23701663
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₉NO₅
Molecular Weight 329.35
Synonym(s) Z-(2S,3R)-AHPA
SMILES O=C(O)[C@@H](O)[C@H](NC(OCC1=CC=CC=C1)=O)CC2=CC=CC=C2

Description

This chiral amino acid derivative features a protected amine and hydroxyl group, enabling direct incorporation into peptide synthesis workflows. The benzyl carbamate moiety provides stable protection under standard conditions, while the phenyl side chain enhances structural rigidity and solubility in organic solvents.

Application

(2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid serves as a key chiral building block for the synthesis of β-lactam antibiotics and peptidomimetic scaffolds. The molecule combines a protected amino group, a labile hydroxyl functionality, and a phenyl-substituted aliphatic chain, enabling selective transformations in peptide coupling and cyclization protocols. Its bench-stable benzyl carbamate protection facilitates purification and orthogonal deprotection, supporting scalable synthesis workflows in medicinal chemistry.

Synthesis

Route1
- 124782-04-3
- ~99%
- In-stock
  
  59969-65-2
References
- Herranz, Rosario; Castro-Pichel, Julia; Garcia-Lopez, Teresa Synthesis, 1989 , # 9 p. 703 - 706
Route2
- 152897-53-5
- ~%
- In-stock
  
  59969-65-2
References
- Kawabata; Kiryu; Sugiura; Fuji Tetrahedron Letters, 1993 , vol. 34, # 32 p. 5127 - 5130
Route3
- 95105-20-7
- ~%
- In-stock
  
  59969-65-2
References
- Fuji, Kaoru; Kawabata, Takeo; Kiryu, Yoshimitsu; Sugiura, Yukio Heterocycles, 1996 , vol. 42, # 2 p. 701 - 722

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 95.86
LogP 1.9696
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoic acid

CAS No. 59969-65-2

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