119323-52-3

Basic information

• Product Name: H-D-THR(TBU)-OH
• Synonyms: O-T-BUTYL-D-THREONINE;H-D-THR(TBU)-OH;H-D-ALLO-THR(TBU)-OH;D-THREONINE(TBU)-OH;D-Thr(tBu)-OH;(2R,3R)-2-Amino-3-(tert-butoxy)butanoic acid;(2R,3R)-2-amino-3-[(2-methylpropan-2-yl)oxy]butanoic acid
• CAS NO: 119323-52-3
• Molecular Formula: C₈H₁₇NO₃
• Molecular Weight: 175.23
• Mol File: 119323-52-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 275.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.055±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.14±0.10(Predicted)
• CAS DataBase Reference: H-D-THR(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-THR(TBU)-OH(119323-52-3)
• EPA Substance Registry System: H-D-THR(TBU)-OH(119323-52-3)

Safety Data

• Hazardous Substances Data: 119323-52-3(Hazardous Substances Data)

Usage

General Description

H-D-THR(TBU)-OH, also known as tert-butyl (2R,3S)-2-amino-3-hydroxybutanoate or D-Threonine, is a form of an amino acid derivative that is typically used in the science and pharmaceutical industries. The t-butyl, or tert-butyl, indicates that it has had a t-butyl protection group added, which makes the chemical less reactive and more stable. This protective group can be removed when necessary during chemical reactions. The “D” suggests that it is the D-isomer, referring to its specific orientation of atoms. OH stands for a hydroxide group, which means this chemical is a specific type of alcohol molecule. H-D-THR(TBU)-OH often appears as a clear, colorless to yellow liquid, and it should be handled carefully due to its potential for causing skin and eye irritation. It plays a vital role in the synthesis of certain pharmaceutical compounds.

Upstream product

• 1227750-69-7 C₉H₁₉NO₃ 
• 4378-13-6 (O-tert-butyl)-L-threonine 

Downstream Products

• 170643-02-4 N^α-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether 

Relevant articles and documents

Effect of the Side Chain on the Racemization of Amino Acids in Aqueous Solution

The rate of racemization of 13 amino acids possessing hydroxy, carboxy, alkoxy, carboalkoxy, alkyl, aryl, and thioether side chains were compared.Reaction conditions were identical for all amino acids studied.Gas chromatography was used to determine the percent of D isomer present.Hydroxy amino acids racemized most rapidly, but conversion to an ether function reduced the rate considerably.The increased racemization rate of methionine (R = CH2CH2SCH3) over Ala (R = CH3) has been attributed to orbital overlap from the sulfur.Asp racemized faster than Glu, α-aminoadipic acid, and pyroglutamic acid. β- and γ-monomethyl esters of aspartic and glutamic acids, respectively, racemized only slightly faster than the corresponding free acids.The slight increase in rate appears attributable to a solvent change brought on by ester hydrolysis.Under the reaction conditions, pH 8 and 140 deg C, hydrolysis of the esters competed favorably with racemization at the methine carbon.The relatively lower racemization rate observed in the case of Glu compared with Asp resulted from the slow formation of pyroglutamic acid.Pyroglutamic acid racemized at a considerably slower rate than acidic amino acids.The differences in the racemization rates with changes in the R group are discussed in terms of several factors, including intramolecular reactions, direct field effects, orbital overlap, and solvation effects, as well as inductive, resonance, and steric factors.