Search results for "Protecting group"

Improved synthesis and application of conjugation-amenable polyols from d-mannose

2019

A series of polyhydroxyl sulfides and triazoles was prepared by reacting allyl and propargyl d-mannose derivatives with selected thiols and azides in thiol-ene and Huisgen click reactions. Conformational analysis by NMR spectroscopy proved that the intrinsic rigidity and linear conformation of the mannose derived polyol backbone is retained in the final click products in solution. Single crystal X-ray structure determination of one of the compounds prepared further verified that the linear conformation of the polyol segment is also retained in the solid state. In addition, an improved method for direct Barbier-type propargylation of unprotected d-mannose is reported. The new reaction protoc…

Redox-Responsive Block Copolymers: Poly(vinylferrocene)-b-poly(lactide) Diblock and Miktoarm Star Polymers and Their Behavior in Solution

2013

The synthesis of diblock and miktoarm star polymers containing poly(vinylferrocene) (PVFc) and poly(l-lactide) (PLA) blocks is introduced. End functionalization of PVFc was carried out via end capping of living carbanionic PVFc chains with benzyl glycidyl ether (BGE). By hydrogenolysis of the benzyl protecting group a dihydroxyl end-functionalized PVFc was obtained. Both monohydroxyl- and dihydroxyl-functionalized PVFcs have been utilized as macroinitiators for the subsequent polymerization of l-lactide via catalytic ring-opening polymerization. A series of block copolymers and AB2 miktoarm star polymers was synthesized with varied PLA chain lengths. All polymers were characterized in detai…

Der (2-Phenyl-2-trimethylsilyl)ethyl-(PTMSE)-Ester – eine neutral spaltbare Carboxyschutzgruppe/The (2-Phenyl-2-trimethylsiylyl)ethyl (PTMSE) Ester –…

2002

(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters of aminoacids and peptides are stable under the conditions of hydrogenolytic cleavage of benzoxycarbonyl(Z) and benzyl ester groups, base-induced removal of Fmoc groups, palladium(0)-catalyzed removal of allyloxycarbonyl (Aloc) and even acidolytic cleavage of Boc groups. PTMSE esters are also stable under the conditions of peptide condensation reactions. The PTMSE ester is selectively cleaved by treatment with tetrabutylammonium fluoride (TBAF) trihydrate in dichloromethane, i. e. under almost neutral conditions, within a few minutes and, therefore, considered a valuable novel carboxy protecting group.

Large Scale Synthesis of Mono- and Di-urethane Derivatives of Lysine.

1999

Orthogonally protected diurethane derivatives of lysine are valuable materials for peptide syntheses. An example is ZLys(Boc), which is exploited in the industrial production of certain well-established peptide drugs. 3,4) Another derivative is Fmoc-Lys(Boc), which is in common use in the laboratory synthesis of peptides. 5) The simplest route to these lysine derivatives seems to be using the copper complex for simultaneous protection of the a-amino and a-carboxyl function, N e -tert-butoxycarbonylation and then copper detachment. The obtained Lys(Boc) might be then subjected to N a -benzyloxycarbonylation.

N-Glycosyl Amides: Removal of the Anomeric Protecting Group and Conversion into Glycosyl Donors.

2003

Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

1992

Abstract The selective synthesis of β- d -mannosides was achieved by first synthesizing β- d -glucosides that carry a N -phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding β- d -mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O -triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired β d -mannoside.

Soluble polymers in organic synthesis

1982

The end function of polyethylene glycol was transferred to the tertiary alcohol for use as acid labile, solubilizing protecting group in peptide synthesis.

The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

2009

New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available.

A five-step synthesis of (±)-tylophorine via a nitrile-stabilized ammonium ylide.

2012

The Stevens rearrangement of a nitrile-stabilized ammonium ylide is the key step of a very short and practical synthesis of the phenanthroindolizine alkaloid (±)-tylophorine. The method requires only five linear steps and is devoid of any protecting group manipulations.

N-{(Z)-2-[1-(Triisopropylsilyl)-1H-indol-3-yl]-2-(triisopropylsilyloxy)vinyl}-2-(3,4,5-trimethoxyphenyl)acetamide

2007

The molecular structure of the title compound, C39H62N2O5Si2, obtained as an unexpected side product, was determined in the course of our studies on the synthesis of N-triisopropyl-1H-indol-3-yl derivatives. Interestingly, although the triisopropylsilyl group was intended as a temporary protecting group, the compound comprises a remarkably stable N—Si bond. The vinyl C=C double bond possesses a Z configuration.