129397-83-7Relevant articles and documents
Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes
Wen, James J.,Crews, Craig M.
, p. 1855 - 1858 (1998)
9-Fluorenylmethoxycarbonyl-protected amino aldehydes could be efficiently prepared in good yields by using two methods: (i) NaBH4 reduction of Fmoc-protected mixed anhydrides, followed by the Swern oxidation of the alcohols; and (ii) LiAlH
Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides
Wenschuh, Holger,Beyermann, Michael,Haber, Hanka,Seydel, Joachim K.,Krause, Eberhard,et al.
, p. 405 - 410 (1995)
The standard methods of stepwise solid phase synthesis according to Merrifield could not previously be applied to the synthesis of the important naturally occurring peptaibols because of difficulties arising from the pronounced steric hindrance caused by α,α-dialkylated amino acids (incomplete coupling, especially to adjacent similarly constituted units, racemization due to slow coupling to hindered amino acids, etc.), chain degradation due to the presence of acid-labile Aib-Pro linkages, and the lack of any general method for the loading of C-terminal amino alcohols to resin supports.Following recent work on model systems, it is now shown that the adoption of Fmoc amino acid fluorides as coupling reagents makes possible the facile, general assembly of such peptides.The method was demonstrated for alamethicin F30 and F50, saturnisporin SA III, and trichotoxin A50J.The crude products were of remarkable purity.Amino acid analysis, mass spectral data, and comparison of the synthetic alamethicins with samples of naturally occurring material confirmed the success of the syntheses.No significant amount of racemization (0.8percent) was found for any of the chiral amino acids present.The first step of the synthesis involved a new general method for assembly of C-terminal peptide alcohols via the use of o-chlorotrityl resin.In addition, model studies on the question of racemization during the coupling of Fmoc amino acid fluorides are reported.
Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides
Alsina, Jordi,Rabanal, Francesc,Chiva, Cristina,Giralt, Ernest,Albericio, Fernando
, p. 10125 - 10152 (1998)
N,N'-disuccinimidyl carbonate (DSC) has been successfully used to generate carbonates and carbamates on conventional hydroxymethyl and aminomethyl based resins. This methodology extends the applicability of such linkers, which were initially designed for
An efficient synthesis of N-protected β-aminoethanesulfonyl chlorides: Versatile building blocks for the synthesis of oligopeptidosulfonamides
Brouwer,Monnee,Liskamp
, p. 1579 - 1584 (2000)
A very efficient method for the synthesis of β-aminoethanesulfonyl chlorides is described. These aliphatic functionalized sulfonyl chlorides are accessible starting from a variety of protected amino acids, including those having functionalized side chains
DMSO-aided o-iodoxybenzoic acid (IBX) oxidation of Fmoc-protected amino alcohols
Chen, Jack J.,Aduda, Vince
, p. 3493 - 3499 (2007)
A fast and highly convenient procedure for the formation of Fmoc-protected amino aldehydes from the corresponding alcohols using 1.1 equiv. of IBX in the presence of dimethylsulfoxide (DMSO) is discussed. This procedure leads to the clean synthesis of Fmo
O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups
Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Suzuki, Tomoyuki,Tamura, Osamu,Tanaka, Kosaku
, p. 899 - 902 (2020/05/28)
Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.
Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
, p. 4874 - 4880 (2018/07/15)
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library
Chen, Ying-Ying,Chang, Li-Te,Chen, Hung-Wei,Yang, Chia-Ying,Hsin, Ling-Wei
, p. 131 - 136 (2017/04/24)
A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino ac
A greener, efficient and catalyst-free ultrasonic-assisted protocol for the n-fmoc protection of amines
Mansouri, Rachida,Aouf, Zineb,Lakrout, Salah,Berredjem, Malika,Aouf, Nour-Eddine
, p. 546 - 550 (2016/03/19)
A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.
Hydrodehalogenation of alkyl iodides with base-mediated hydrogenation and catalytic transfer hydrogenation: Application to the asymmetric synthesis of N-protected α-methylamines
Mandal, Pijus K.,Birtwistle, J. Sanderson,McMurray, John S.
, p. 8422 - 8427 (2015/03/18)
We report a very mild synthesis of N-protected α-methylamines from the corresponding amino acids. Carboxyl groups of amino acids are reduced to iodomethyl groups via hydroxymethyl intermediates. Reductive deiodination to methyl groups is achieved by hydrogenation or catalytic transfer hydrogenation under alkaline conditions. Basic hydrodehalogenation is selective for the iodomethyl group over hydrogenolysis-labile protecting groups, such as benzyloxycarbonyl, benzyl ester, benzyl ether, and 9-fluorenyloxymethyl, thus allowing the conversion of virtually any protected amino acid into the corresponding N-protected α-methylamine.
