IX.—Syntheses of glucosides. Part VII. The synthesis of 6-bromoindican

Robertson, Alexander; Waters, Roy Basil

doi:10.1039/jr9310000072

Cited by 6 publications

(7 citation statements)

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“…The very first syntheses of indicane and 5-bromo-indicane, were published by Robertson already in 1927 and 1929 15,16 . By employing indoxylic acid methyl ester as acceptor, the reactive 2-position was blocked and thus side reactions were partially suppressed.…”

Section: Representative Resultsmentioning

confidence: 99%

“…Finally the acetyl protecting groups were removed (16) according to Zemplén employing sodium methanolate in anhydrous methanol. This way a three step glycosylation procedure gave the final indoxyl galactopyranoside component (16) in 66% overall yield. In a former attempt the synthesis of a corresponding indoxyl galactopyranoside resulted in 28% yield 6 .…”

Section: Representative Resultsmentioning

confidence: 99%

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Böttcher

Thiem

2015

JoVE

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Indoxyl glycosides proved to be valuable and versatile tools for monitoring glycosidase activities. Indoxyls are released by enzymatic hydrolysis and are rapidly oxidized, for example by atmospheric oxygen, to indigo type dyes. This reaction enables fast and easy screening in vivo without isolation or purification of enzymes, as well as rapid tests on agar plates or in solution (e.g., blue-white screening, micro-wells) and is used in biochemistry, histochemistry, bacteriology and molecular biology. Unfortunately the synthesis of such substrates proved to be difficult, due to various side reactions and the low reactivity of the indoxyl hydroxyl function. Especially for glucose type structures low yields were observed. Our novel approach employs indoxylic acid ester as key intermediates. Indoxylic acid esters with varied substitution patterns were prepared on scalable pathways. Phase transfer glycosylations with those acceptors and peracetylated glycosyl halides can be performed under common conditions in high yields. Ester cleavage and subsequent mild silver mediated glycosylation yields the peracetylated indoxyl glycosides in high yields. Finally deprotection is performed according to Zemplén. Video LinkThe video component of this article can be found at

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Section: Representative Resultsmentioning

confidence: 99%

Section: Representative Resultsmentioning

confidence: 99%

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Böttcher

Thiem

2015

JoVE

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“…The thermal decomposition of NH 4 NO 3 was previously studied. [130][131][132][133][134] An initial decomposition step involves an endothermic reaction where NH 4 NO 3 dissociates to nitric acid and ammonia. [130][131][132]134] An exothermic reaction can decompose NH 4 NO 3 into nitrous oxide and H 2 O.…”

Section: Tntmentioning

confidence: 99%

Review of explosive detection methodologies and the emergence of standoff deep UV resonance Raman

Gares

Hufziger

Bykov

et al. 2016

J Raman Spectroscopy

102

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Due to terrorist use of explosive devices, intense interest has been directed towards the development of techniques and instrumentation to detect explosives. A number of analytical techniques are currently under investigation for trace explosive detection. Several methods have been successfully commercialized including colorimetric kits, fluorescence quenching sensors, and ion mobility spectrometers that see widespread field use. A key limitation of all currently utilized field techniques is that they require close proximity or physical interaction with the object being analyzed. The ideal trace explosive detection technique would be able to detect trace amounts of explosives from a distance to ensure personnel safety. Laser‐based spectroscopies are the only currently viable techniques that can be utilized to sense trace amounts of explosives at standoff distances. This review compares currently used explosive detection techniques with recently developed standoff methods. We emphasize the development of UV resonance Raman spectroscopy for standoff explosive detection. This work has recently been enabled by advances in laser and spectrometer design. Trace explosive detection has also been advanced by the recently developed understanding of deep UV photochemistry for several explosive molecules. Copyright © 2016 John Wiley & Sons, Ltd.

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“…The procedures presented above have not been used subsequently to prepare Tyrian purple, but the individual reactions have been used for synthesis of the precursors 43 [ 50 , 125 , 126 , 127 , 128 , 129 ], 46 [ 125 , 129 , 130 , 131 , 132 ] and 48 [ 130 , 131 , 132 ].…”

Section: Preparation Of Tyrian Purple From 4-bromo-2-aminobenzoic mentioning

confidence: 99%