(2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate

Name: (2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate
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CAS No. 79479-07-5
Cat. No. CS-W014677
Purity≥95%
MDL No.MFCD00270479

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(2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate|CS-W014677

Structure of 79479-07-5

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General Information

CAS No. 79479-07-5
Cat. No. CS-W014677
Purity ≥95%
MDL No. MFCD00270479
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₉NO₅
Molecular Weight 233.26
Synonym(s) N-BOC-L-threonine methylester
SMILES C[C@@H](O)[C@@H](C(OC)=O)NC(OC(C)(C)C)=O

Description

This chiral diester features a protected amino acid scaffold with defined stereochemistry at C2 and C3, enabling precise incorporation into peptide syntheses. The tert-butyl carbamate group ensures stability during manipulations, while the hydroxyl functionality offers a handle for selective derivatization. Designed for use in advanced synthetic routes requiring controlled reactivity and configurational integrity.

Application

(2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate serves as a stereochemically defined chiral building block for the synthesis of β-hydroxy amino acid derivatives and peptidomimetics. The protected amine and hydroxyl groups enable orthogonal functionalization, while the methyl ester facilitates downstream transformations. Its bench-stable nature and compatibility with standard coupling and reduction protocols make it well-suited for iterative peptide synthesis and medicinal chemistry applications.

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 84.86
LogP 0.4335
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 3

Other Classifications

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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(2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate

CAS No. 79479-07-5

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