(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Name: (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 13500-53-3
Cat. No. CS-0156263
Molecule weight355.39
Purity≥97%
MDL No.MFCD12407103

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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate|CS-0156263

Structure of 13500-53-3

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General Information

CAS No. 13500-53-3
Cat. No. CS-0156263
Purity ≥97%
MDL No. MFCD12407103
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₁NO₅
Molecular Weight 355.39
Synonym(s) (2S,4R)-1,2-Dicarbobenzyloxy-4-hydroxypyrrolidine
SMILES C1=CC=C(C=C1)COC(=O)[C@@H]2C[C@H](CN2C(=O)OCC3=CC=CC=C3)O

Description

This chiral pyrrolidine derivative features a dibenzyl-protected 4-hydroxypyrrolidine scaffold with defined stereochemistry at the 2S,4R positions. The molecule integrates a hydroxyl group and two benzyl ester functionalities, enabling selective deprotection and downstream coupling in asymmetric synthesis. Bench-stable and compatible with standard peptide and small-molecule workflows, it serves as a high-fidelity building block for complex natural product and pharmaceutical intermediates.

Application

(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate serves as a stereochemically defined chiral building block for the synthesis of pyrrolidine-based scaffolds. The protected hydroxyl and dibenzyl ester functionalities enable selective transformations, including deprotection, derivatization, and coupling reactions. Its stability under standard bench conditions and compatibility with diverse reaction protocols facilitate efficient access to complex heterocycles and bioactive molecules in medicinal chemistry and process development workflows.

Synthesis

Route1
- 100-39-0
- In-stock
  
  13504-85-3
- ~99%
- In-stock
  
  13500-53-3
References
- Giacalone, Francesco; Gruttadauria, Michelangelo; Lo Meo, Paolo; Riela, Serena; Noto, Renato Advanced Synthesis and Catalysis, 2008 , vol. 350, # 17 p. 2747 - 2760
Route2
- In-stock
  
  13139-17-8
- 88501-00-2
- ~80%
- In-stock
  
  13500-53-3
References
- Agarkov, Anton; Greenfield, Scott J.; Ohishi, Takahiro; Collibee, Scott E.; Gilbertson, Scott R. Journal of Organic Chemistry, 2004 , vol. 69, # 23 p. 8077 - 8085
Route3
- 541-41-3
- In-stock
  
  100-51-6
- In-stock
  
  13504-85-3
- ~70%
- In-stock
  
  13500-53-3
References
- Calderon, Felix; Fernandez, Raquel; Sanchez, Felix; Fernandez-Mayoralas, Alfonso Advanced Synthesis and Catalysis, 2005 , vol. 347, # 10 p. 1395 - 1403

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

TPSA 76.07
LogP 2.5018
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate

CAS No. 13500-53-3

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