Synthesis of Fmoc-Protected Amino Ketones Bearing tert-Butyl Based Side-Chain Protecting Groups.

ChemInform ◽  
2003 ◽  
Vol 34 (3) ◽  
Author(s):  
Jesus Vazquez ◽  
Fernando Albericio
Keyword(s):  
Protecting Groups ◽  
Side Chain ◽  
Tert Butyl

Synthese eines Thymosin β10-Fragments zur Entwicklung spezifischer Antikörper / Synthesis of a Fragment of Thymosin β10 for the Development of Specific Antibodies

1992 ◽  
Vol 47 (8) ◽  
pp. 1170-1174 ◽  
Author(s):  
Susanne Hörger ◽  
Brigitte Gallert ◽  
Hartmut Echner ◽  
Wolfgang Voelter
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Protecting Groups ◽  
Side Chain ◽  
Phase Method ◽  
Preparative Hplc ◽  
Specific Antibodies ◽  
Tert Butyl ◽  
Thymosin Β10 ◽  
Solid Phase Method

The N-terminal fragment 1-12 of thymosin β10 was synthesized by the solid phase method using p-benzyloxybenzyl alcohol/polystyrene/divinylbenzeneresin and N-a-Fmoc amino acids with tert-butyl or Boc side chain protecting groups. Coupling was performed with BOP. The peptide was purified by preparative HPLC.

scholarly journals Phenylthiazoles with tert-Butyl side chain: Metabolically stable with anti-biofilm activity

2018 ◽  
Vol 151 ◽  
pp. 110-120 ◽  
Author(s):  
Ahmed Kotb ◽  
Nader S. Abutaleb ◽  
Mohamed A. Seleem ◽  
Mohamed Hagras ◽  
Haroon Mohammad ◽  
...  
Keyword(s):  
Side Chain ◽  
Tert Butyl

Bis(ether) derivatives of tetrakis(2-hydroxyphenyl)ethene — Direct synthesis of (E)- and (Z)-bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene via the McMurry olefination reaction

2006 ◽  
Vol 84 (10) ◽  
pp. 1250-1253 ◽  
Author(s):  
Mee-Kyung Chung ◽  
Paul Fancy ◽  
Jeffrey M Stryker
Keyword(s):  
Supramolecular Chemistry ◽  
Direct Synthesis ◽  
Protecting Groups ◽  
Tert Butyl ◽  
Orthogonal Protection ◽  
Protection Strategies ◽  
Titanium Trichloride ◽  
Sterically Hindered ◽  
Derivatives Of

The direct synthesis of sterically hindered, partially etherified derivatives of tetrakis(2-hydroxyphenyl)ethene is reported by using the McMurry reductive olefination reaction on a range of differentially substituted 2,2′-dialkoxy benzophenone substrates. Three orthogonal protection strategies are demonstrated, incorporating β-silylethyl, 3-butenyl, and tert-butyl protecting groups, respectively, into the starting benzophenones. The latter proved most efficient, with both the McMurry coupling and deprotection steps occurring concomitantly under the McMurry conditions to directly yield the desired bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene as a 1:1 mixture of E- and Z-diastereoisomers.Key words: preorganized polyaryloxide ligands, McMurry olefination, titanium trichloride, supramolecular chemistry, tetrakis(2-hydroxyphenyl)ethene, 2,2′-disubstituted benzophenone.

Synthesis of thymosin α1 by fragment condensation using tert.-butyl side chain protection

2009 ◽  
Vol 26 (2) ◽  
pp. 130-148 ◽  
Author(s):  
ARTHUR M. FELIX ◽  
EDGAR P. HEIMER ◽  
CHING-TSO WANG ◽  
THEODORE J. LAMBROS ◽  
JOSEPH SWISTOK ◽  
...  
Keyword(s):  
Side Chain ◽  
Thymosin Α1 ◽  
Tert Butyl ◽  
Fragment Condensation

The tert-Butyl Side Chain: A Powerful Means to Lock Peptoid Amide Bonds in the Cis Conformation

2013 ◽  
Vol 15 (9) ◽  
pp. 2246-2249 ◽  
Author(s):  
O. Roy ◽  
C. Caumes ◽  
Y. Esvan ◽  
C. Didierjean ◽  
S. Faure ◽  
...  
Keyword(s):  
Side Chain ◽  
Amide Bonds ◽  
Tert Butyl ◽  
Powerful Means

Zur Totalsynthese des Human-Big-Gastrins I und seines 32-Leucin-Analogons (Vorläufige Mitteilung) / Total Synthesis of Human Big Gastrin I and the 32-Leucine Analogue (Preliminary Communication)

1977 ◽  
Vol 32 (7-8) ◽  
pp. 495-506 ◽  
Author(s):  
E. Wünsch ◽  
G. Wendlberger ◽  
A. Hallett ◽  
E. Jaeger ◽  
S. Knof ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Building Blocks ◽  
Ion Exchange Chromatography ◽  
Exchange Chromatography ◽  
Protecting Groups ◽  
Side Chain ◽  
Tertiary Alcohols ◽  
Synthetic Product ◽  
Preliminary Communication ◽  
Final Purification

A new total synthesis of the tetratriacontapeptide amide corresponding to the proposed primary structure of human big gastrin I is described. The synthetic route was based on the preparation of six suitably protected fragments, related to sequence 28 - 34, 23 - 27, 21 - 22, 15-20, 9 - 14, and 1 - 8, to be used as building blocks for the total synthesis. The protecting groups were selected according to the Schwyzer-Wünsch strategy of maximum side chain protection based on tertiary alcohols, also for the imidazol function of histidine. Subsequent assembly of the six fragments by three different pathways using the highly efficient Wünsch-Weygand condensation procedure to ensure minimum racemization, followed by deprotection of the synthetic products via exposure to trifluoroacetic acid and final purification by ion-exchange chromatography on DEAE-Sephadex A-25 and partition chromatography on Sephadex G-25, led to human big gastrin I, homogeneous within the limits of the analytical methods used. The biological activity of the synthetic product proved to be 50 percent higher than that of human little gastrin I. The 32-leucine analogue of human big gastrin I was prepared in the same way.

PREPARATION AND PROPERTIES OF Nα-9-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS BEARING TERT.-BUTYL SIDE CHAIN PROTECTION

2009 ◽  
Vol 15 (1) ◽  
pp. 59-66 ◽  
Author(s):  
CHI-DEU CHANG ◽  
MICHINORI WAKI ◽  
MUSHTAQ AHMAD ◽  
JOHANNES MEIENHOFER ◽  
EDWIN O. LUNDELL ◽  
...  
Keyword(s):  
Side Chain ◽  
Tert Butyl

Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4683-4689 ◽  
Author(s):  
Mark Trudell ◽  
Ryan McKinnie ◽  
Tasneam Darweesh ◽  
Phoebe Zito ◽  
Terrell Shields
Keyword(s):  
Efficient Method ◽  
Synthetic Cannabinoids ◽  
Synthetic Cannabinoid ◽  
Protecting Groups ◽  
Side Chain ◽  
Hydroxy Metabolites

An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting groups for epoxidation and regioselective hydrofluorination. The 1-[5-fluoro-4-(diphenyl-tert-butylsilyloxy)]pentyl tosylate was prepared in 67% overall yield (six steps) from pent-4-en-1-ol and was employed for the synthesis of the 4-hydroxy metabolites of the synthetic cannabinoid 5F-APINACA and CUMYL-5F-PINACA.

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