Boc-3-(1-naphthyl)-L-alanine
Need Assistance?
  • US & Canada:
    +
  • UK: +

Boc-3-(1-naphthyl)-L-alanine

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

Boc-3-(1-naphthyl)-L-alanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Category
BOC-Amino Acids
Catalog number
BAT-007956
CAS number
55447-00-2
Molecular Formula
C18H21NO4
Molecular Weight
315.36
Boc-3-(1-naphthyl)-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-1-ylpropanoic acid
Synonyms
Boc-L-Ala(1-naphthyl)-OH; Boc-(S)-2-amino-3-(naphthalen-1-yl)propanoic acid; Boc-3-(1-naphthyl)-L-alanine; Boc-L-1-naphthylalanine; Boc-1-Nal-OH; (S)-N-Boc-L-(1-naphthyl)alanine; (2S)-2-[(tert-butoxy)carbonylamino]-3-naphthylpropanoic acid; Boc-L-3-(1-Naphthyl)-alanine; Boc L Nal OH
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.200 g/cm3
Melting Point
144 °C
Boiling Point
512.2 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-13-9-6-8-12-7-4-5-10-14(12)13/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1
InChI Key
KHHIGWRTNILXLL-HNNXBMFYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=CC2=CC=CC=C21)C(=O)O
1.Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines.
Kano T1, Kobayashi R1, Maruoka K1. Org Lett. 2016 Jan 15;18(2):276-9. doi: 10.1021/acs.orglett.5b03446. Epub 2016 Jan 4.
Previously inaccessible N-Boc-protected propargylic and allylic amines were synthesized by the reaction between N-Boc-aminals and organomagnesium reagents through the in situ generated N-Boc-imine intermediates. The obtained N-Boc-propargylic amines could be readily converted into unprecedented N-Boc-ketimines by oxidation with manganese dioxide.
2.Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines.
Smith JJ1, Best D1, Lam HW1. Chem Commun (Camb). 2016 Feb 25;52(19):3770-2. doi: 10.1039/c6cc00603e.
Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.
3.Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates.
Lim DS1, Lew TT1, Zhang Y1. Org Lett. 2015 Dec 18;17(24):6054-7. doi: 10.1021/acs.orglett.5b03061. Epub 2015 Nov 25.
N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
Online Inquiry
Verification code
Inquiry Basket