(S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid

Name: (S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
Brand: ChemScene
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CAS No. 88784-33-2
Cat. No. CS-0156250
Molecule weight367.35
Purity≥95%
MDL No.MFCD13152207

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(S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid|CS-0156250

Structure of 88784-33-2

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General Information

CAS No. 88784-33-2
Cat. No. CS-0156250
Purity ≥95%
MDL No. MFCD13152207
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₁₇NO₆
Molecular Weight 367.35
Synonym(s) 5-Benzyl (S)-2-phthalimidoglutarate
SMILES C1=CC=C(C=C1)COC(=O)CC[C@@H](C(=O)O)N2C(=O)C3=CC=CC=C3C2=O

Description

This chiral β-keto acid integrates a benzyl ether handle and isoindoline-1,3-dione motif, enabling direct conjugation in peptide synthesis. The pendant benzyloxy group facilitates orthogonal protection, while the electron-deficient isoindolinone enhances reactivity in nucleophilic addition cascades. Bench-stable under standard conditions, it streamlines access to complex heterocyclic scaffolds.

Application

(S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid serves as a versatile chiral building block for the synthesis of complex heterocyclic scaffolds. Its functionality enables efficient Michael additions and cyclization reactions, leveraging the orthogonality of the benzyloxy and dioxoisoindolinyl groups. The molecule exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic workflows in medicinal chemistry and process development.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 100.98
LogP 2.2594
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

88784-33-2 sigma88784-33-2 manufacturer88784-33-2 price88784-33-2 structure88784-33-2 SDSbuy 88784-33-288784-33-2 supplier88784-33-2 uses88784-33-2 molecular weightprice of 88784-33-288784-33-2 chemical name formula of 88784-33-2

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(S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid

CAS No. 88784-33-2

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