N-Boc-D-proline

Name: N-Boc-D-proline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 37784-17-1
Cat. No. CS-D0669
Purity≥98%
MDL No.MFCD00063226

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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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Structure of 37784-17-1

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General Information

CAS No. 37784-17-1
Cat. No. CS-D0669
Purity ≥98%
MDL No. MFCD00063226
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₇NO₄
Molecular Weight 215.25
Synonym(s) None
SMILES O=C(OC(C)(C)C)N(CCC1)[C@H]1C(O)=O

Description

N-Boc-D-proline features a stable tert-butoxycarbonyl-protected amine and a chiral pyrrolidine ring, enabling reliable incorporation into peptide synthesis and asymmetric catalysis. This bench-stable derivative facilitates efficient coupling reactions under standard conditions while maintaining stereochemical integrity during iterative transformations.

Application

N-Boc-D-proline serves as a versatile chiral building block in asymmetric synthesis, enabling efficient construction of pyrrolidine-containing scaffolds. The Boc group provides excellent stability and ease of removal under mild acidic conditions, while the D-proline moiety offers predictable stereocontrol in enantioselective catalysis and peptide coupling. Its functional group tolerance and compatibility with standard coupling reagents make it ideal for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  344-25-2
- ~98%
- In-stock
  
  37784-17-1
References
- Andries, Julien; Lemoine, Laetitia; Le Bars, Didier; Zimmer, Luc; Billard, Thierry European Journal of Medicinal Chemistry, 2011 , vol. 46, # 8 p. 3455 - 3461
Route2
- 124-38-9
- In-stock
  
  86953-79-9
- ~55%
- In-stock
  
  37784-17-1
References
- Fournier, Anne M.; Brown, Robert A.; Farnaby, William; Miyatake-Ondozabal, Hideki; Clayden, Jonathan Organic Letters, 2010 , vol. 12, # 10 p. 2222 - 2225
Route3
- 1294505-66-0
- ~79%
- In-stock
  
  37784-17-1
References
- Ghosh, Partha; Aube, Jeffrey Journal of Organic Chemistry, 2011 , vol. 76, # 10 p. 4168 - 4172

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 66.84
LogP 1.4705
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Life Science Amino Acids and their Derivatives Proline and derivatives

Building Blocks Functional Group Boc

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural 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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N-Boc-D-proline

CAS No. 37784-17-1

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