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Hydroboration. 97. Synthesis of New Exceptional Chloroborane−Lewis Base Adducts for Hydroboration. Dioxane−Monochloroborane as a Superior Reagent for the Selective Hydroboration of Terminal Alkenes†


09 Dec 2016

Equivalency of reagents key for successful synthesis

Review: Synthesized the same compound of Dioxane-Monochloroborane by the reaction of Sodium Borohydride with Dioxane-borontrichloride (experimental section, Page 5364). I found the equivalency of the reagents is very important for this reaction. The reaction...

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Construction of the Bicyclo[3.1.0]hexane Template of a Conformationally Locked Carbocyclic Adenosine via an Olefin Keto-Carbene Cycloaddition


09 Dec 2016

Experimental Yields Lower than Literature

Victor E. Marquez et. al. first introduced the concept of locked conformations, 2'-exo (North) and 3'-exo (South), of ribose ring in nucleosides. In this article the synthetic methodology and successful synthesis of receamic and conformationally locked South...

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Enantiomers of 1-ethyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid: preparation and biological activity


09 Dec 2016

Procedure Adapted for Better Synthesis

Wanting to avoid a chromatographic separation of the Me esters as well as the greater expense of dimethyl itaconate, the reaction of alpha methyl benzylamine and itaconic acid was performed in xylene.  The reaction was performed by adding the amine at 110 to...

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Catalytic Isomerization of Cyanoolefins Involved in the Adiponitrile Process. C−CN Bond Cleavage and Structure of the Nickel π-Allyl Cyanide Complex Ni(η3-1-Me-C3H4)(CN)(dppb)


09 Dec 2016

Helpful experimental; Some discrepancies observed in NMR

The article reports the catalytic isomerization of the branched cyanoolefin 2-methyl-3-butenenitrile (2M3BN) to the linear isomer 3-pentenenitrile (3PN) using nickel-phosphine complexes.

The authors report that the optimal catalytic experiment was carried...

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Isolation and reactions of .alpha.-lithio N,N-dimethylacetamide


09 Dec 2016

Reproducible Experimental

Summary: The paper discusses the synthesis, reactivity and stability of α-lithio N,N dimethylacetamide.

The paper described carefully the use of various solvents (pentane, THF) and their impact on the formation of the desired product.

It also described...

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A Convenient Synthesis of Novel Bifunctional Prochelators for Coupling to Bioactive Peptides for Radiometal Labelling


09 Dec 2016

Extremely helpful and reliable paper

 

Summary

The article describes the synthesis of cyclen based chelators which can accommodate and stabilize di-and trivalent metal ions for biomedical applications. The chelators were synthesized first by monoalkylating cyclen (1,4,7,10...

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DIPHENALDEHYDE


09 Dec 2016

Reliable Procedure

The procedure described in this paper is very reliable. The ozone should be used in a fully functional fume hood as described.

1. Synthesized 10.1 g of crude diphenaldehyde starting from 10.0 g of phenanthrene.

2. The crude 1H-NMR of product is 80%...

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Selective Bromination of Perylene Diimides under Mild Conditions


09 Dec 2016

Good experimental, some modification to work-up

In this paper, selective bromination of perylene diimides is described. I was able to reproduce the bromination of 1a. However, the workup involves evaporating large volumes of bromine. I was able to isolate similar yields of products by quenching the...

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Enantioselective formation of functionalized 1,3-disubstituted allenes: synthesis of .alpha.-allenic .omega.-carbomethoxy alcohols of high optical purity


09 Dec 2016

Few Experimental Modifications Implemented to Improve Yield

Synthesized (3) and a compound similar to (4) but with protection on -OH groups. 

For (3): Dissolving CBr4 in dichloromethane instead of pyridine gave a better yield as it involved using only one solvent throughout the reaction. 

For (4): The formation...

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Synthesis and reactions of the cyclic silyl peroxide 1,1,4,4-tetramethyl-2,3-dioxa-1,4-disilacyclohexane


09 Dec 2016

Exact Procedure Not Provided By Authors

Summary:

The first simple cyclic silyl peroxide, namely 1,1,4,4,-tetramethyl-1,4-disila-2,3-dioxane, was prepared by classical synthetic methodology from its corresponding cyclic disilazane and the urea complex of hydrogen peroxide.

The Reaction of...

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Total Synthesis of the Hsp90 Inhibitor Geldanamycin


09 Dec 2016

Amazingly short synthesis for complex macrolide

This paper describes amazingly shortest synthesis for such a complex macrolide. Geldanamycin was synthesized in 20 steps using key steps such as Cu-catalyzed intramolecular amidation. I have used synthetic strategy to synthesize prodrug of geldanamycin with...

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On a new synthesis of sterpurene and the bioactivity of some related Chondrostereum purpureum sesquiterpene metabolites


09 Dec 2016

Reliable procedure but modifications helpful

The article by Strunz and co-workers reported a total synthesis of sterpurene and the bioactivity of some related sesquiterpene metabolites.

I am particularly interested in the preparation of intermediate 14 (4-step synthesis, Scheme 3) since it could...

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Facile Synthesis of Structurally Diverse 3,3′-Disubstituted 1,1′-Binaphthyl-2,2′-diamines in Optically Pure Forms


09 Dec 2016

Simple BINAM ligand synthesis,improvements made for scale-up

Maruoka et al. developed a new synthetic route to access 3,3’-disubstituted BINAM compounds which are nitrogen derivatives of popular axial chiral ligands BINOL and BINAP. Their multi step approach involves in partial hydrogenation of BINAM to H8-BINAM,...

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Quinazoline antifolate thymidylate synthase inhibitors: heterocyclic benzoyl ring modifications


09 Dec 2016

Reproducible on smaller scale

Synthesized 2-[N-( tert -Butoxycarbonyl)amino]thiophene (25) and a similar compound (2-[N-( tert -Butoxycarbonyl)amino]-5-bromothiophene) following the same procedure described in the article as method F.

For the synthesis of 25, the reaction was scaled...

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Desymmetrization Reactions:  Efficient Preparation of Unsymmetrically Substituted Linker Molecules


09 Dec 2016

Innovative,one-pot method to synthesize bifunctional linkers

The paper presents an innovative way to synthesis bi functional linker (in this case azido-amine linkers). The method used described as concurrent reaction-extraction taking place in one pot has attracted a lot of attention. In the synthesis of compound 1 a...

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Toward Optimized High-Relaxivity MRI Agents:  The Effect of Ligand Basicity on the Thermodynamic Stability of Hexadentate Hydroxypyridonate/Catecholate Gadolinium(III) Complexes


09 Dec 2016

Tweaks Necessary to Improve Yield

Summary:

This paper describes the synthesis of a new hydroxypyridinone applicable for MRI technology. The basicity was measured and related to the thermodynamic stability with Gd.

 

Reaction of interest:

Our interest was the formation of the ring...

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Asymmetric synthesis of (−)-α-conhydrine


09 Dec 2016

Exp. Modification Necessary to Address Variable Yield

In one of my recent projects, I need find a method to convert diethyl malonate-d2 into 3-bromopropanol-d6. Following a literature reported procedure (Eur. J. Org. Chem. 2011, 3339–3346), diethyl malonate-d2 underwent lithium aluminum deuteride (LAD) reduction...

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Nickel-Catalyzed Isomerization of 2-Methyl-3-butenenitrile†


09 Dec 2016

Modifications to catalytic isomerization of 2M3BN to 3PN

This article reports the catalytic isomerization of the branched isomer 2-methyl-3-butenenitrile (2M3BN) to the linear isomer 3-pentenenitrile (3PN) by DPEphos nickel species.

The species involved in the isomerization reaction were investigated by...

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Dramatic enhancement of carrier mobility via effective secondary structural arrangement resulting from the substituents in a porphyrin transistor


09 Dec 2016

Thorough study of porphyrin transistor derivatives

Enhancement of carrier mobility due to a secondary structural arrangement resulting from the substituents in a porphyrin transistor was observed. OSCFETs based on two different porphyrin derivatives displayed excellent mobilities of 2.57 and 0.48 cm2 V-1 s-1....

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pH-Dependent Si-Fluorescein Hypochlorous Acid Fluorescent Probe: Spirocycle Ring-Opening and Excess Hypochlorous Acid-Induced Chlorination


09 Dec 2016

Novel and less expensive Hypo-SiF synthesis

  • Hypo-SiF is uniquely new in finding the high concentration of HOCl
  • Hypo-SiF is reported to be good in finding the HOCl concentration and pH of the media simultaneously at lower concentrtion
  • To obtain clear results, Hypo-SiF needs to be improved and...

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