(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Name: (R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 6404-31-5
Cat. No. CS-M0865
Purity≥98%
MDL No.MFCD00063228

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid|CS-M0865

Structure of 6404-31-5

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General Information

CAS No. 6404-31-5
Cat. No. CS-M0865
Purity ≥98%
MDL No. MFCD00063228
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₅NO₄
Molecular Weight None
Synonym(s) Z-D-Pro-OH
SMILES O=C(OCC1=CC=CC=C1)N(CCC2)[C@H]2C(O)=O

Description

(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid features a chiral pyrrolidine core with a benzylcarbamate protecting group, enabling selective incorporation into peptide sequences. This bench-stable derivative delivers precise stereochemical control in synthetic peptide workflows and supports efficient coupling under standard conditions.

Application

(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of peptidomimetics and bioactive heterocycles. Its benzyloxycarbonyl (Cbz) group provides orthogonal protection for the amine, enabling selective deprotection during peptide coupling sequences. The pyrrolidine-2-carboxylic acid scaffold exhibits excellent functional group tolerance and bench stability, facilitating efficient incorporation into complex molecular architectures via standard amide bond formation and catalytic transformations.

Synthesis

Route1
- 501-53-1
- In-stock
  
  344-25-2
- ~%
- In-stock
  
  6404-31-5
References
- Journal of Pharmaceutical Sciences, , vol. 80, # 9 p. 837 - 842
Route2
- 99464-81-0
- In-stock
  
  344-25-2
- ~90%
- In-stock
  
  6404-31-5
References
- Barcelo, Gerard; Senet, Jean-Pierre; Sennyey, Gerard; Bensoam, Jean; Loffet, Albert Synthesis, 1986 , # 8 p. 627 - 632
Route3
- 50463-82-6
- ~90%
- In-stock
  
  6404-31-5
References
- Mazzini, Claudio; Sambri, Letitia; Regeling, Henk; Zwanenburg, Binne; Chittenden, Gordon J. F. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 22 p. 3351 - 3356

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-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 66.84
LogP 1.8722
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

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

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid

CAS No. 6404-31-5

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