(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

Name: (S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid
Brand: ChemScene
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CAS No. 91028-39-6
Cat. No. CS-0468262
Purity≥97%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid|CS-0468262

Structure of 91028-39-6

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General Information

CAS No. 91028-39-6
Cat. No. CS-0468262
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₅NO₄
Molecular Weight 201.22
Synonym(s) Boc-L-vinylglycine
SMILES CC(C)(C)OC(N[C@@H](C=C)C(O)=O)=O

Description

(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid is a chiral building block featuring a vinyl carboxylic acid moiety flanked by a protected amine. This structure enables direct incorporation into peptide backbones and facilitates subsequent deprotection under mild acidic conditions. The tert-butyl carbamate group provides excellent stability during synthetic manipulations, while the electron-rich alkene supports efficient coupling reactions.

Application

(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid serves as a versatile chiral building block for the synthesis of bioactive peptides and heterocyclic scaffolds. The protected amino group enables orthogonal functionalization, while the α,β-unsaturated carboxylic acid moiety facilitates conjugate additions and cycloaddition reactions. Its bench-stable tert-butyl carbamate protection simplifies purification and supports scalable synthesis in medicinal chemistry workflows.

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 75.63
LogP 1.1503
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Life Science Amino Acids and their Derivatives Alanine and derivatives

Building Blocks Functional Group Boc

Building Blocks Functional Group Olefins

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-((tert-Butoxycarbonyl)amino)but-3-enoic acid

CAS No. 91028-39-6

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