(3R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid

Name: (3R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid
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CAS No. 203854-51-7
Cat. No. CS-0035706
Purity≥97%
MDL No.MFCD01862865

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(3R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid|CS-0035706

Structure of 203854-51-7

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General Information

CAS No. 203854-51-7
Cat. No. CS-0035706
Purity ≥97%
MDL No. MFCD01862865
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₇NO₅
Molecular Weight 397.46
Synonym(s) Fmoc-β-HoSer(tBu)-OH
SMILES CC(C)(OC[C@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)CC(O)=O)C

Description

This fluoren-9-ylmethyl carbamate-protected amino acid derivative features a sterically hindered tert-butyl ether group and a chiral (3R) center, enabling reliable incorporation into peptide sequences. The fluorenylmethoxycarbonyl (Fmoc) moiety provides orthogonal protection, while the pendant tert-butoxy functionality enhances solubility and stability under standard coupling conditions.

Application

(3R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid serves as a robust, bench-stable chiral building block for peptide synthesis and medicinal chemistry applications. Its structure combines a C-terminal tert-butyl ester with a fluorenylmethoxycarbonyl (Fmoc) protected amine, enabling orthogonal deprotection during solid-phase peptide synthesis. The molecule exhibits excellent functional group tolerance and facilitates efficient coupling reactions under standard conditions, supporting high-yield assembly of complex peptide sequences and peptidomimetic scaffolds.

Synthesis

Route1
- 203854-41-5
- ~71%
- In-stock
  
  203854-51-7
References
- Vasanthakumar; Babu, V. V. Suresh Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003 , vol. 42, # 7 p. 1691 - 1695
Route2
- In-stock
  
  71989-33-8
- ~%
- In-stock
  
  203854-51-7
References
- Helvetica Chimica Acta, , vol. 81, # 2 p. 187 - 206

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 88.35
LogP 4.3879
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(3R)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]butanoic acid

CAS No. 203854-51-7

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