(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate

Name: (R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate
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CAS No. 149709-59-1
Cat. No. CS-0009329
Molecule weight409.52
Purity≥98%
MDL No.MFCD23378892

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(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate|CS-0009329

Structure of 149709-59-1

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General Information

CAS No. 149709-59-1
Cat. No. CS-0009329
Purity ≥98%
MDL No. MFCD23378892
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₃₁NO₄
Molecular Weight 409.52
Synonym(s) None
SMILES [H]/C([C@@H](CC(C=C1)=CC=C1C2=CC=CC=C2)N(C(OC(C)(C)C)=O)[H])=C(C(OCC)=O)/C

Description

(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate features a chiral α,β-unsaturated ester framework with a bulky biphenyl substituent and a protected amine. This bench-stable building block integrates readily into asymmetric synthesis workflows, enabling efficient access to complex biaryl-containing peptidomimetics and pharmaceutical intermediates under standard conditions.

Application

(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate serves as a versatile chiral building block for the synthesis of biologically relevant heterocycles and peptidomimetics. Its conjugated enoate moiety enables efficient Michael additions and Diels–Alder reactions, while the Boc-protected amine offers orthogonal handling. The molecule exhibits excellent bench stability, facilitates straightforward deprotection, and supports functional group tolerance in multi-step synthetic sequences.

Synthesis

Route1
- In-stock
  
  149709-58-0
- 21382-82-1
- ~79%
- In-stock
  
  149709-59-1
References
- Ksander, Gary M.; Ghai, Raj D.; deJesus, Reynalda; Diefenbacher, Clive G.; Yuan, Andrew; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 10 p. 1689 - 1700

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 64.63
LogP 5.2988
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Olefins

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate

CAS No. 149709-59-1

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