Search results for "Protecting group"
showing 10 items of 54 documents
FeCl3·6H2O-catalyzed Mukaiyama-aldol type reactions of enolizable aldehydes and acetals.
2014
Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3·6H2O, an eco-friendly, low-cost, and stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3·6H2…
Fluorous TBAF: A Convenient and Selective Reagent for Fluoride-Mediated Deprotections
2009
A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.
Die 2-(Triphenylphosphonio)isopropyloxycarbonyl-(Ppoc-)-Gruppe und am Phosphoniumzentrum modizifierte analoge Reste als Aminoschutzgruppen bei der Pe…
1985
Die Einfuhrung in Aminosauren, die Stabilitat bei Peptidsynthesen und die selektive Abspaltung der 2-(Triphenylphosphonio)isopropyloxycarbonyl-(Ppoc-)-Aminoschutzgruppe sowie ihrer Varianten mit (Methyl)(diphenyl)phosphonium- und (Dimethyl)(phenyl)phosphoniumkopfen werden beschrieben. Der Ppoc-Rest ist in etwa um den Faktor 4 basenstabiler als der entsprechende 2-(Triphenylphosphonio)ethoxycarbonyl-(Peoc-)Rest. Er kann dennoch bereits bei pH = 8 in wasrig-methanolischer Hydrogencarbonatlosung von der blockierten Aminofunktion abgelost werden. Im Gegensatz zur Peoc-Abspaltung treten dabei keine storenden Nebenreaktionen des entstehenden Propenylphosphoniumsalzes mit der freigesetzten Aminofu…
ChemInform Abstract: The Allyl Ester as Carboxy-Protecting Group in the Stereoselective Construction of Neuraminic Acid Glycosides.
1989
The application of the allyl-ester moiety as protecting principle for the carboxy group of N-acetylneuraminic acid is described. Peracetylated allyl neuraminate 2 is synthesized by reacting the caesium salt of the acid 1 with allyl bromide. Treatment of 2 with HCl in AcCl or with HF/pyridine gives the corresponding 2-chloro or 2-fluoro derivatives 3 and 4, respectively (Scheme 1). In the presence of Ag2CO3, the 2-chloro carbohydrate 3 reacts with di-O-isopropylidene-protected galactose 5 to give the 2–6 linked disaccharide with the α-D-anomer 6a predominating (α-D/β-D = 6:1; Scheme 2). Upon activation of the 2-fluoro derivative 4 with BF3 · Et2O, the β-D-anomer 6b is formed preferentially (…
ChemInform Abstract: Differential Reactivity of Fluorinated Homopropargylic Amino Esters vs Gold(I) Salts. The Role of the Nitrogen Protecting Group.
2015
The gold(I)-catalyzed hydroarylation/isomerization reaction of N-protected homopropargyl amino esters (III) gives quinoline derivatives of type (IV).
Stereoselective synthesis of glycosides and anomeric azides of glucosamine
1992
The β-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phasetransfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluorid…
ChemInform Abstract: Stereoselective Synthesis of Glycosides and Anomeric Azides of Glucosamine.
2010
The β-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phasetransfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluorid…
Efficient preparation of 4-methoxy-5,6-dihydro-2H-pyran
2008
Abstract We report the efficient synthesis of 4-methoxy-5,6-dihydro-2 H -pyran (MDHP) via the TiCl 4 driven elimination of MeOH from 4,4-dimethoxytetrahydropyran. The previous difficulty of preparing MDHP restricted the wider use of 4-methoxytetrahydropyran-4-yl (MTHP) acyclic acetals, which have desirable protecting group properties when compared to more commonly used MOM- and THP-acetals. The behaviour of the elimination on related acetals is also examined.
Red- and Blue-Shifts in Oligo(1,4-phenyleneethynylene)s Having Terminal Donor−Acceptor Substitutions
2004
Four series of oligo(1,4-phenyleneethynylene)s (OPEs), 1−4 (a−d), each having a terminal dialkylamino group as their electron donor, were prepared by applying Sonogashira−Hagihara reactions and a protecting group strategy. To study the influence that the push−pull effect has on the long-wavelength absorption, three of the four series of OPEs contain terminal acceptor groups (CN, CHO, NO2). Extending the conjugation (increasing the number of repeat units, n) lowers the energy E(n) of the electron transition in the purely donor-substituted series 1a−4a (bathochromic shift). This effect is superimposed in the push−pull series 1−4 (b−d) by the effect of the intramolecular charge transfer (ICT),…
Der 2-(4-pyridyl)Ethoxycarbonyl-(4-Pyoc)-rest - eine hydrophile, säure- und basenstabile aminoschutzgruppe für die peptidsynthese
1984
Abstract The title amino blocking function is stable under basic and acidic conditions frequently used in the peptide synthesis. Its hydrophilicity permits an effective peptide synthesis in water. After the easy conversion to the pyridinium form the 4-Pyoc group can be removed by morpholine.