N-Z-L-proline methyl ester

Name: N-Z-L-proline methyl ester
Brand: ChemScene
Availability: InStock
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CAS No. 5211-23-4
Cat. No. CS-0015967
Purity≥96%
MDL No.MFCD00134246

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 5211-23-4

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General Information

CAS No. 5211-23-4
Cat. No. CS-0015967
Purity ≥96%
MDL No. MFCD00134246
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇NO₄
Molecular Weight 263.29
Synonym(s) 1,2-Pyrrolidinedicarboxylic acid, 2-methyl 1-(phenylmethyl) ester, (S)-; Methyl (S)-N-(benzyloxycarbonyl)prolinate
SMILES O=C(OC)[C@H]1N(C(OCC2=CC=CC=C2)=O)CCC1

Description

N-Z-L-proline methyl ester delivers a chiral proline scaffold with enhanced solubility and stability, enabling efficient incorporation into peptide syntheses. The methyl ester group facilitates direct coupling without activation, while the Z-protected nitrogen ensures regioselective reaction control under standard conditions. This reagent streamlines access to complex peptidomimetics and constrained cyclic architectures.

Application

N-Z-L-proline methyl ester serves as a robust chiral building block in asymmetric synthesis, enabling efficient construction of pyrrolidine-based scaffolds and peptidomimetics. Its Z-protected amine and methyl ester functionality offer enhanced stability and orthogonal reactivity, facilitating selective transformations in multi-step sequences. The molecule's defined stereochemistry supports high enantioselectivity in catalytic reactions, making it a practical choice for medicinal chemistry campaigns requiring configurational control.

Synthesis

Route1
- 67-56-1
- In-stock
  
  1148-11-4
- ~99%
- In-stock
  
  5211-23-4
References
- Pfeifer, Marc E.; Linden, Anthony; Robinson, John A. Helvetica Chimica Acta, 1997 , vol. 80, # 5 p. 1513 - 1527
Route2
- 67-56-1
- 61350-60-5
- ~89%
- In-stock
  
  5211-23-4
References
- Nakatsuji, Hidefumi; Morimoto, Mami; Misaki, Tomonori; Tanabe, Yoo Tetrahedron, 2007 , vol. 63, # 48 p. 12071 - 12080
Route3
- 147-85-3
- ~%
- In-stock
  
  5211-23-4
References
- Ni, Yike; Zhao, Gang; Ding, Yu Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 19 p. 3264 - 3266

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
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 55.84
LogP 1.9606
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-Z-L-proline methyl ester

CAS No. 5211-23-4

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