(S)-2,5-Dioxopyrrolidin-1-yl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate

Name: (S)-2,5-Dioxopyrrolidin-1-yl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate
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CAS No. 30189-36-7
Cat. No. CS-W011597
Purity≥97%
MDL No.MFCD00057898

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(S)-2,5-Dioxopyrrolidin-1-yl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate|CS-W011597

Structure of 30189-36-7

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General Information

CAS No. 30189-36-7
Cat. No. CS-W011597
Purity ≥97%
MDL No. MFCD00057898
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₃₃N₃O₈
Molecular Weight 443.49
Synonym(s) Boc-Lys(Boc)-OSu
SMILES O=C(ON1C(CCC1=O)=O)[C@H](CCCCNC(OC(C)(C)C)=O)NC(OC(C)(C)C)=O

Description

This chiral dipeptide derivative features a (S)-configured pyrrolidinone core paired with two tert-butoxycarbonyl-protected amino groups, enabling selective coupling in peptide synthesis. The orthogonal protection facilitates sequential elongation while maintaining stereochemical integrity under standard conditions.

Application

(S)-2,5-Dioxopyrrolidin-1-yl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate serves as a versatile dipeptide coupling reagent, enabling efficient amide bond formation under mild conditions. The molecule features two orthogonal tert-butyl carbamate-protected amino groups flanking a central aliphatic chain, facilitating sequential peptide elongation. Its pyrrolidinone ester moiety ensures high reactivity with nucleophiles while maintaining bench stability and ease of purification. Functions reliably in solid-phase and solution-phase peptide synthesis, particularly for constructing complex oligopeptides and cyclic scaffolds.

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

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Computational Chemistry Data

TPSA 140.34
LogP 2.1819
H_Acceptors 8
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2,5-Dioxopyrrolidin-1-yl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate

CAS No. 30189-36-7

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