Facile Synthesis of Benzyl Alcohol Type Hypercrosslinked Resin

2011 ◽  
Vol 239-242 ◽  
pp. 868-871
Author(s):  
Qiu Jin ◽  
Pu Hui Xie ◽  
Lin Xiu Zhao ◽  
Ling Ling Bai ◽  
Si Guo Yuan
Keyword(s):  
Benzyl Alcohol ◽  
Pore Diameter ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
High Specific Surface Area ◽  
The Novel ◽  
Average Pore ◽  
Hydroxymethyl Group ◽  
Phase Synthesis ◽  
Adsorption Resin

A kind of novel hypercrosslinked resin containing hydroxymethyl group was firstly synthesised via chloromethylation of benzyl alcohol monomer and succedent Friedel- Crafts alkylation polymerization. The structure and micromorphology of the resin was characterized with BET, IR and elemental analysis. The results indicated that the novel polar adsorption resin possess high specific surface area (525.00m2/g) and abundant micropore structure (average pore diameter: 1.123nm), and could be anticipated having a potential application in the fields of solid phase synthesis, separation and adsorption.

scholarly journals Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1872 ◽  
Author(s):  
Ondřej Kostov ◽  
Radek Liboska ◽  
Ondřej Páv ◽  
Pavel Novák ◽  
Ivan Rosenberg
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Novel ◽  
Phase Synthesis ◽  
Chimeric Oligonucleotides ◽  
Modified Oligonucleotide

We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands.

scholarly journals Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

2016 ◽  
Vol 12 ◽  
pp. 2556-2562 ◽  
Author(s):  
Elisabeth Mairhofer ◽  
Elisabeth Fuchs ◽  
Ronald Micura
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
The Novel ◽  
Facile Synthesis ◽  
Phase Synthesis

Access to 3-deazaadenosine (c3A) building blocks for RNA solid-phase synthesis represents a severe bottleneck in modern RNA research, in particular for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, we report the 5-step synthesis of a c3A phosphoramidite from cost-affordable starting materials. The key reaction is a silyl-Hilbert–Johnson nucleosidation using unprotected 6-amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling.

scholarly journals The solid phase synthesis of tertiary hydroxyesters from symmetrical diacid chlorides using organomanganese reagents

1980 ◽  
Vol 58 (3) ◽  
pp. 287-290 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Varda Yedidia
Keyword(s):  
Benzyl Alcohol ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Styrene Copolymer

A 1% crosslinked divinylbenzene–styrene copolymer, incorporating benzyl alcohol groups, was used to monoblock the symmetrical diacid chlorides, ClOC(CH2)nCOCl (where n = 4 and 8). Further reaction of the polymer-bound monoester monoacid chloride with phenylmanganese iodide or butylmanganese iodide gave their respective polymer-bound tertiary hydroxyesters. Subsequent base cleavage and esterification yielded methyl 6-hydroxy-6, 6-diphenylhexanoate, methyl 10-hydroxy-10,10-diphenyldecanoate, methyl 6-butyl-6-hydroxydecanoate, and methyl 10-butyl-10-hydroxytetradecanoate and some recovered dimethyl alkanoates. The reactions of some polymer-bound monoester monoacid chlorides with phenylcadmium chloride were also studied.

scholarly journals Synthesis of the Novel Covalent Cysteine Proteases Inhibitor with Iodoacetic Functional Group

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 813 ◽  
Author(s):  
Kinga Hartman ◽  
Przemyslaw Mielczarek ◽  
Jerzy Silberring
Keyword(s):  
Mass Spectrometry ◽  
Functional Group ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Cysteine Proteases ◽  
Iodoacetic Acid ◽  
The Novel ◽  
Phase Synthesis ◽  
Fmoc Solid Phase Synthesis ◽  
Covalent Inhibitor

This work presents the synthesis of the novel covalent inhibitor of cysteine proteases where epoxide has been replaced by the iodoacetyl functional group. The molecule, similar in action to E-64 and DCG-04, the commonly applied inhibitors, is additionally biotinylated and contains tyrosyl iodination sites. The Fmoc solid phase synthesis has been applied. Conjugation of iodoacetic acid with the peptide was optimized by testing different conjugation agents. The purity of the final product was verified by mass spectrometry and its bioactivity was tested by incubation with a model cysteine protease—staphopain C. Finally, it was shown that the synthesized inhibitor binds to the protein at the ratio of 1:1. More detailed analysis by means of tandem mass spectrometry proved that the inhibitor binds to the cysteine present in the active site of the enzyme.

The solid phase synthesis of monoester monoamides and monoester monoalcohols from symmetrical diacid chlorides

1978 ◽  
Vol 56 (11) ◽  
pp. 1562-1568 ◽  
Author(s):  
Judah M. Goldwasser ◽  
Clifford C. Leznoff
Keyword(s):  
Benzyl Alcohol ◽  
Good Yield ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Borohydride Reduction ◽  
Subsequent Reaction ◽  
Terephthaloyl Chloride ◽  
Phase Synthesis ◽  
Tert Butylamine ◽  
Isophthaloyl Chloride

A 2% crosslinked divinylbenzene–styrene copolymer, incorporating benzyl alcohol groups, was used to monoprotect the symmetrical diacid chlorides, ClOC(CH2)nCOCl (where n = 2, 3, 4, and 8), terephthaloyl chloride and isophthaloyl chloride. Subsequent reaction of the resulting polymer-bound monoester monoacid chloride with aniline, benzylamine, dimethylamine, tert-butylamine, or ammonia yielded polymer-bound monoester monoamides, which on base cleavage and esterification gave monoester monoamides inhighyield. Borohydride reduction of polymer-bound sebacoyl chloride, terephthaloyl chloride, and isophthaloyl chloride gave their respective polymer-bound monoester monoalcohols, which on base cleavage from the polymer and esterification yielded the monoester monoalcohols in good yield along with some recovered dimethyl esters of the respective starting diacid chlorides.

Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones

RSC Advances ◽  
2016 ◽  
Vol 6 (14) ◽  
pp. 11528-11535 ◽  
Author(s):  
Ajjampura C. Vinayaka ◽  
Toreshettahally R. Swaroop ◽  
Prasanna Kumara Chikkade ◽  
Kanchugarakoppal S. Rangappa ◽  
Maralinganadoddi P. Sadashiva
Keyword(s):  
Transition Metal ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Novel ◽  
Phase Synthesis ◽  
Metal Free

The transition-metal-free economical solid phase synthesis of 1,2-disubstituted 4-quinolones has been developed via the novel regiospecific synthesis of enaminones.

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