Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

Sakaitani, Masahiro; Ohfune, Yasufumi

doi:10.1021/jo00290a015

Cited by 274 publications

(137 citation statements)

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“…NMR spectra were measured in CDCl 3 or DMSO-d 6 at 200 MHz for protons and 50 MHz for 13 C, and recorded on a Bruker AC-200 spectrometer. Infrared spectra were taken on a Beckman AccuLab 8 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Furlán¹,

Mata²

2003

Arkivoc

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Section: Methodsmentioning

confidence: 99%

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Furlán¹,

Mata²

2003

Arkivoc

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“…Es gelang aber mit Hilfe von TBSOTf, die BocGruppe chemoselektiv in das Silylcarbamat 148 umzuwandeln (Schema 3.16). [211,212] …”

Section: Kupplung Der Fragmenteunclassified

Totalsynthese von Nosiheptid

Wojtas

Riedrich

et al. 2016

Angewandte Chemie

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Eine Totalsynthese des bismakrocyclischen Thiopeptidantibiotikums Nosiheptid gelang durch den Aufbau einer voll funktionalisierten linearen Vorstufe und konsekutive Makrocyclisierungen. Schlüsselmerkmale waren eine kritische Makrothiolactonisierung und eine milde Entschützungsstrategie für den 3‐Hydroxypyridin‐Kern. Der Naturstoff war mit isoliertem authentischem Material im Hinblick auf spektroskopische Daten und antimikrobielle Aktivität identisch.

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“…Yield 65%, R f = 0.51 (10% chloroform/methanol), ODVAD). Due to the presence of a double bond between C 9 -C 10 acyl chains of the oleoyl derivative, the benzyl chloroformate (Cbz) group was deprotected using triethylsilane and palladium (II) chloride, as shown in Scheme 2 [12]. Briefly, dibenzyl {[(N, N'-dioleoyl-1, 3-diaminopropyl-2-oxycarbonyl) imino] diethane-2, 1-diyl} biscarbamate 19 (1.75 g, 2.13 mmol) was dissolved in anhydrous chloroform (20 mL) under dry nitrogen.…”

Section: N N'-dilauroyl-13-diaminopropyl-2-[bis-(2-aminoethyl)] Carmentioning

confidence: 99%

Synthesis, Biophysical Characterization and <i>in Vitro</i> Transfection Activity of Novel Bivalent Amine Cationic Lipids in the Absence of Dioleoylphosphatidylethanolamine (DOPE)

Donkor¹,

Spelios²,

Savva³

2014

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In this paper, a novel series of bis [(aminoethyl)]-amine cationic lipid derivatives have been synthesized and identified to purity by NMR and Elemental analysis. B16-F0 cells were transfected with cationic lipid/pEGFP-N1 and cationic lipid/β-gal lipoplexes complexed at +/− charge ratios of 1:1, 2:1, and 4:1. Dimyristoyl derivative showed highest activity at charge ratio 2:1 and both dimyristoyl and dioleoyl derivatives showed similar β-gal activity at charge ratios 4:1. In 40 mM tris buffer pH 7.2 the dioleoyl derivative was able to fully complex with and retard pDNA at charge ratios above 2:1. None of the other lipid derivatives, dilauroyl, dimyristoyl, dipalmitoyl and distearoyl were able to fully neutralize the plasmid DNA at charge ratios similar to those used in the transfection experiment. The gel-to-liquid phase transition temperatures for dimyristoyl, dipalmitoyl and distearoyl were determined by a fluorescence anisotropy method to be 27.5˚C, 32.5˚C and 39˚C, respectively. A gel-to-liquid crystalline phase transition temperature below 37˚C, appears to be the crucial property that cationic lipids have to possess in order to mediate high levels of in vitro transfection activity in the absence of other helper lipids.

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Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

Cited by 274 publications

References 0 publications

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Totalsynthese von Nosiheptid

Synthesis, Biophysical Characterization and <i>in Vitro</i> Transfection Activity of Novel Bivalent Amine Cationic Lipids in the Absence of Dioleoylphosphatidylethanolamine (DOPE)

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Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

Cited by 274 publications

References 0 publications

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Totalsynthese von Nosiheptid

Synthesis, Biophysical Characterization and &lt;i&gt;in Vitro&lt;/i&gt; Transfection Activity of Novel Bivalent Amine Cationic Lipids in the Absence of Dioleoylphosphatidylethanolamine (DOPE)

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Synthesis, Biophysical Characterization and <i>in Vitro</i> Transfection Activity of Novel Bivalent Amine Cationic Lipids in the Absence of Dioleoylphosphatidylethanolamine (DOPE)