(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Name: (2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 122350-59-8
Cat. No. CS-M3064
Purity≥97%
MDL No.MFCD12545917

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(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate|CS-M3064

Structure of 122350-59-8

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General Information

CAS No. 122350-59-8
Cat. No. CS-M3064
Purity ≥97%
MDL No. MFCD12545917
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₁NO₅
Molecular Weight 367.40
Synonym(s) None
SMILES O=C(OC)[C@@H]1C[C@@H](O)CN1C(OCC2C3=C(C=CC=C3)C4=C2C=CC=C4)=O

Description

This chiral pyrrolidine derivative features a fluorenylmethyl-protected amine and a hydroxyl group at C4, enabling selective functionalization in asymmetric synthesis. The 2-methyl substitution enhances stereochemical stability, while the bench-stable protecting group facilitates handling under standard conditions.

Application

(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate serves as a versatile chiral building block for the synthesis of pyrrolidine-based scaffolds. Its hydroxyl group enables selective derivatization, while the fluorenylmethyl (Fmoc) protecting group ensures stability and facilitates purification. The molecule functions effectively in peptide coupling and heterocycle formation, offering high diastereoselectivity and compatibility with standard synthetic workflows.

Synthesis

Route1
- In-stock
  
  40216-83-9
- In-stock
  
  82911-69-1
- ~96%
- In-stock
  
  122350-59-8
References
- Liu, Hongqiang; Pattabiraman, Vijaya R.; Vederas, John C. Organic Letters, 2007 , vol. 9, # 21 p. 4211 - 4214
Route2
- In-stock
  
  82911-69-1
- 1499-56-5
- ~86%
- In-stock
  
  122350-59-8
References
- Lewis, Ian; Bauer, Wilfried; Albert, Rainer; Chandramouli, Nagarajan; Pless, Janos; Weckbecker, Gisbert; Bruns, Christian Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2334 - 2344
Route3
- In-stock
  
  40216-83-9
- In-stock
  
  88744-04-1
- ~%
- In-stock
  
  122350-59-8
References
- Chemistry - A European Journal, , vol. 15, # 40 p. 10649 - 10657

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 76.07
LogP 2.5437
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Fmoc

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

CAS No. 122350-59-8

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