Methyl benzyl-L-serinate

Name: Methyl benzyl-L-serinate
Brand: ChemScene
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CAS No. 123639-56-5
Cat. No. CS-0146698
Molecule weight209.24
Purity≥98%
MDL No.MFCD07367716

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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 123639-56-5

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General Information

CAS No. 123639-56-5
Cat. No. CS-0146698
Purity ≥98%
MDL No. MFCD07367716
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅NO₃
Molecular Weight 209.24
Synonym(s) None
SMILES COC([C@H](CO)NCC1=CC=CC=C1)=O

Description

Methyl benzyl-L-serinate is a chiral amino acid derivative featuring a methyl ester and benzyl-protected hydroxyl group. This configuration enhances solubility in organic solvents while maintaining stability under standard bench conditions. The molecule integrates readily into peptide synthesis workflows, enabling efficient access to serine-containing sequences with high diastereoselectivity.

Application

Methyl benzyl-L-serinate serves as a versatile chiral building block in peptide synthesis, offering controlled stereochemistry and enhanced solubility. Its ester functionality enables straightforward derivatization, while the benzyl group provides stability and facilitates purification. The molecule functions effectively in amide coupling reactions and is compatible with standard protecting group strategies, making it well-suited for the synthesis of bioactive peptides and complex heterocyclic scaffolds.

Synthesis

Route1
- In-stock
  
  5680-80-8
- 100-52-7
- ~85%
- In-stock
  
  123639-56-5
References
- Loh, Teck-Peng; Chok, Yew-Keong; Yin, Zheng Tetrahedron Letters, 2001 , vol. 42, # 44 p. 7893 - 7897
Route2
- 40216-75-9
- ~%
- In-stock
  
  123639-56-5
References
- Tetrahedron Letters, , vol. 31, # 34 p. 4917 - 4920 Phosphorus, Sulfur and Silicon and Related Elements, , vol. 160, p. 223 - 232
Route3
- 2788-84-3
- 100-52-7
- ~84%
- In-stock
  
  123639-56-5
References
- Shiokawa, Zenyu; Hashimoto, Kentaro; Saito, Bunnai; Oguro, Yuya; Sumi, Hiroyuki; Yabuki, Masato; Yoshimatsu, Mie; Kosugi, Yohei; Debori, Yasuyuki; Morishita, Nao; Dougan, Douglas R.; Snell, Gyorgy P.; Yoshida, Sei; Ishikawa, Tomoyasu Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 24 p. 7938 - 7954

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 58.56
LogP 0.3101
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Serine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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Methyl benzyl-L-serinate

CAS No. 123639-56-5

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