BOC-THR(ME)-OH

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Cat Number

INT48068253

CAS Number

48068-25-3

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Product Detail Description Customer Q&A

CAS Number

48068-25-3

Storage

2-8℃

Synonyms

BOC-O-METHYL-L-THREONINE;(2S,3R)-2-(tert-butoxycarbonylamino)-3-methoxybutanoic acid

Molecular Formula

C10H19NO5

Molecular Weight

233.26

Smiles

C(O)(=O)[C@H]([C@H](OC)C)NC(OC(C)(C)C)=O

Appearance

White to off-white solid

Boiling Point

362.1℃

Relative Density

1.123

pKa

3.5

General Description

BOC-THR(ME)-OH is an N-alpha-Boc protected derivative of L-threonine where the secondary hydroxyl group on the side chain is modified as a methyl ether. This modification is crucial for maintaining the integrity of the threonine residue during complex synthetic routes.

Mechanism of Action

It functions as a protected monomer in peptide chemistry. The methyl ether on the side chain acts as a permanent protecting group that withstands the conditions of peptide chain elongation, while the Boc group allows for orthogonal deprotection strategies essential for multi-step organic synthesis.

Application

It is widely applied in the synthesis of peptidomimetics, glycopeptide analogs, and other modified peptides where a non-reactive threonine side chain is necessary to avoid side reactions.