Fmoc-O-tert-Butyl-D-trans-4-hydroxyproline

Name: Fmoc-O-tert-Butyl-D-trans-4-hydroxyproline
Brand: ChemScene
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CAS No. 268729-12-0
Cat. No. CS-0187839
Purity≥95%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Fmoc-O-tert-Butyl-D-trans-4-hydroxyproline|CS-0187839

Structure of 268729-12-0

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General Information

CAS No. 268729-12-0
Cat. No. CS-0187839
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₇NO₅
Molecular Weight 409.47
Synonym(s) (2R,4S)-4-(1,1-Dimethylethoxy)-1,2-Pyrrolidinedicarboxylic Acid 1-(9H-Fluoren-9-Ylmethyl) Ester
SMILES CC(C)(C)O[C@H]1C[C@H](C(=O)O)N(C1)C(=O)OCC2C3=C(C=CC=C3)C4=C2C=CC=C4

Description

Fmoc-O-tert-butyl-D-trans-4-hydroxyproline features a D-trans-4-hydroxyproline core protected at the hydroxyl group with a tert-butyl moiety and at the amine with an Fmoc group. This bifunctional derivative enables direct incorporation into peptide chains during solid-phase synthesis, offering enhanced solubility and stability under standard conditions. The trans configuration ensures defined stereochemistry, critical for structural integrity in bioactive peptide design.

Application

Fmoc-O-tert-butyl-D-trans-4-hydroxyproline serves as a key chiral building block in peptide synthesis, enabling the incorporation of D-proline derivatives with defined stereochemistry. The Fmoc group provides orthogonal protection for the amine, while the O-tert-butyl ether stabilizes the 4-hydroxyl functionality under standard coupling conditions. This derivative exhibits excellent bench stability, facilitates efficient purification, and supports high-yielding amide bond formation in solid-phase and solution-phase 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-P280-P302+P352

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Computational Chemistry Data

TPSA 76.07
LogP 4.2781
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Ether

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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Fmoc-O-tert-Butyl-D-trans-4-hydroxyproline

CAS No. 268729-12-0

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