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Application Area

N-Boc-D-alaninol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(R)-2-(Boc-amino)-1-propanol (CAS# 106391-86-0) is a useful research chemical.

Category

BOC-Amino Acids

Catalog number

BAT-014399

CAS number

106391-86-0

Molecular Formula

C8H17NO3

Molecular Weight

175.23

IUPAC Name

tert-butyl N-[(2R)-1-hydroxypropan-2-yl]carbamate

Synonyms

Boc-D-Ala-ol; N-tert-butoxycarbonyl-D-alaninol; (R)-2-(Boc-amino)-1-propanol; (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate; (R)-(+)-2-(tert-Butoxycarbonylamino)-1-propanol; Carbamic acid, [(1R)-2-hydroxy-1-methylethyl]-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl [(2R)-1-hydroxy-2-propanyl]carbamate

Appearance

White Powder

Purity

≥95%

Density

1.025±0.06 g/cm3 (Predicted)

Melting Point

58-61°C

Boiling Point

276.4±23.0°C (Predicted)

Storage

Store at -20°C

InChI

InChI=1S/C8H17NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)/t6-/m1/s1

InChI Key

PDAFIZPRSXHMCO-ZCFIWIBFSA-N

Canonical SMILES

CC(CO)NC(=O)OC(C)(C)C

N-Boc-D-alaninol, a specialized chemical compound with wide-ranging applications, is instrumental in various research and industrial settings. Here are the key applications of N-Boc-D-alaninol presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a crucial building block in peptide and protein synthesis, N-Boc-D-alaninol plays a pivotal role in the creation of diverse molecules. The N-Boc protecting group ensures stability throughout the intricate process of peptide chain assembly, facilitating meticulous and controlled synthesis. This compound is indispensable for generating peptides utilized in a myriad of applications, from pharmaceutical research to the development of diagnostic kits and therapeutic interventions.

Chiral Synthesis: Within the realm of chiral synthesis, N-Boc-D-alaninol emerges as a key component for producing enantiomerically pure compounds. Its incorporation into chemical reactions enhances stereoselectivity, streamlining the attainment of desired enantiomers in significant quantities. This application holds paramount importance in the synthesis of optically active drugs and substances with specific biological activities, driving advancements in medicinal chemistry and pharmaceutical sciences.

Pharmaceutical Intermediates: Widely employed as an intermediate in pharmaceutical synthesis, N-Boc-D-alaninol facilitates the creation of diverse pharmaceutical compounds. Its unique structure enables straightforward functional group modifications, empowering chemists to craft complex molecules critical for drug development. This versatility positions it as a cornerstone in medicinal chemistry, supporting the production of active pharmaceutical ingredients (APIs) vital for addressing medical needs and improving healthcare outcomes.

Organic Chemistry Research: Positioned at the forefront of organic chemistry research, N-Boc-D-alaninol fuels mechanistic studies and synthetic transformations. Researchers leverage this compound to delve into novel reaction pathways, driving the evolution of synthetic methodologies. Its application in research propels the understanding of chemical processes, fostering innovation in material science and pharmaceutical discovery.

1. Synthesis of 3-(3-pyridyl)- and 3-(3-benzo[b]thienyl)-D-alanine

P N Rao, J E Burdett Jr, J W Cessac, C M DiNunno, D M Peterson, H K Kim Int J Pept Protein Res. 1987 Jan;29(1):118-25. doi: 10.1111/j.1399-3011.1987.tb02237.x.

The DL-arylamino acid ethyl ester derivatives of beta-(3-pyridyl)-DL-alanine, and beta-(3-benzo[b]thienyl)-DL-alanine were synthesized by diethyl acetamidomalonate condensation with the respective arylmethyl halides followed by partial hydrolysis to the monoethyl ester and decarboxylation. Each derivative was enzymatically resolved to a separable mixture of the corresponding N-acetyl-L-amino acid and the unchanged D amino acid derivative. Acidic hydrolysis of the latter gave the corresponding D-amino acid, the optical purity of which was established by HPLC analysis of the 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) derivative. The free D amino acids were converted to D-BOC derivatives by reaction with di-tert-butyldicarbonate in tert-butyl alcohol, water and sodium hydroxide.

2. Electrospray ionization tandem mass spectrometry of protonated and alkali-cationized Boc-N-protected hybrid peptides containing repeats of D-Ala-APyC and APyC-D-Ala: formation of [b(n-1) + OCH3 + Na]+ and [b(n-1) + OH + Na]+ ions

G Raju, C Purna Chander, K Srinivas Reddy, R Srinivas, G V M Sharma Rapid Commun Mass Spectrom. 2012 Nov 30;26(22):2591-600. doi: 10.1002/rcm.6381.

Rationale: Differentiation and structural characterization of positional isomers of non-natural amino acid hybrid peptides by using electrospray ionization tandem mass spectrometry (ESI-MS(n) ) is desirable because of their fundamental importance from the view point of peptide mass spectrometry and also of their increasing importance in the area of research towards biomedical and material applications; hence, the present study is undertaken. Methods: Electrospray ionization ion-trap tandem mass spectrometry (ESI-MS(n)) was used to characterize and differentiate three pairs of positional isomers of Boc-N-protected hybrid peptides containing repeats of D-Ala-APyC and APyC-D-Ala (D-Ala = D-alanine and APyC = trans-3-aminopyran-2-carboxylic acid). Results: ESI-MS(n) spectra of protonated and alkali-cationized positional isomeric peptides display characteristic fragmentation involving the peptide backbone, the Boc group, and the side chain. It is observed that abundant rearrangement ions [b(n-1) + OCH(3) + Na](+) or [b(n-1) + OH + Na](+) are formed when D-Ala is present at C-terminus and the presence of APyC at the C-terminus inhibits the formation of rearrangement ions. In addition, abundant b(n-1)(+) ions are formed, presumably with stable oxazolone structures, when the C-terminus of b(n-1) (+) ions possessed D-Ala. Conclusions: The present study demonstrates that ESI tandem mass spectrometry is very useful for differentiating positional isomers of hybrid peptides containing D-Ala and APyC amino acids. While the protonated peptides give rise to characteristic sequencing ions, the cationized peptides produce additional rearrangement ions ([b(n-1) + OCH(3) + Na](+) and [b(n-1) + OH + Na](+)) which helps distinguish between the presence of D-Ala and APyC amino acids at the C-terminus.

3. Synthesis of novel d-α-galactopyranosyl-l-seryl/l-threonyl-l-alanyl-l-alanine as useful precursors of new glycopeptide antibiotics with computational calculations studies

Ahmed I Khodair, Shaymaa E Kassab, Nabila A Kheder, Asmaa M Fahim Carbohydr Res. 2022 Apr;514:108546. doi: 10.1016/j.carres.2022.108546. Epub 2022 Mar 28.

New, simple, synthetic routes for the preparation of novel glycopeptide antibiotics are described. The structures of the synthesized compounds are elucidated by IR, two-dimensional NMR spectroscopy, and mass spectrometry. The stability of the new glycopeptide derivatives 10a,b is confirmed by assessing the physical character, HOMO-LUMO gap energy, ESP, and the corresponding correlation of 2D-NMR analysis. Furtherly, the target precursors are investigated via the DFT/B3LYP/6-311(G) basis set.