Straightforward S–S Bond Formation via the Oxidation of S-Acetyl by Iodine in the Presence of N-Iodosuccinimide

Ge, Jiantao; Zhou, Lang; Zhao, Fu-Long; Dong, Hai

doi:10.1021/acs.joc.7b02367

Cited by 21 publications

(20 citation statements)

References 58 publications

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“…While there are advantages to using these platform materials, paper brings its own inherent advantages and has also been used for separation. Recently both proteins [94] and small molecules [95] have been separated using paper-based devices. Metal ion complexes have also been detected and their electrochromatographic separation in a paper-based device was presented by OuYang et al [96].…”

Section: Electrophoresis and Isotachophoresismentioning

confidence: 99%

Electrochemical paper‐based microfluidic devices

2015

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Self-pumping porous microfluidic devices have attracted significant interest because of their low cost and broad applicability in point-of-care and low resource settings. One limitation of many of the devices is sensitivity and selectivity for detection. Electrochemistry can provide a sensitive, selective detection method while still using low cost, portable instrumentation as typified by handheld glucometers. Here, the development of electrochemical paper-based analytical devices (ePADs) is reviewed. Given the importance of electrode geometry and composition, fabrication methods are reviewed first. This is followed by a review of example applications demonstrated for ePADs. Finally, major accomplishments and future directions are summarized.

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Section: Electrophoresis and Isotachophoresismentioning

confidence: 99%

Electrochemical paper‐based microfluidic devices

2015

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“…In our previous studies on the synthesis of deoxyglycosides by desulfurization under UV light (Ge et al, 2017b(Ge et al, , 2019, we didn't obtain 4-deoxymannosidic derivatives because we were unable to obtain 4-SAc mannosides efficiently. With 4-SAc mannosides 5 and 6 in the hands, 4-deoxymannosidic derivatives 46 and 47 were obtained in 81 and 79% yields by our one-pot method removing thioacetate group (Figure 2), respectively.…”

Section: Resultsmentioning

confidence: 99%

Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration

Luo

Zhang

et al. 2020

Front. Chem.

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Complex mixtures were often observed when we attempted to synthesize 4-thio-and 2,4-dithio-glycoside derivatives by double parallel and double serial inversion, thus leading to no or low yields of target products. The reason was later found to be that many unexpected side products were produced when a nucleophile substituted the leaving group on the substrate containing the thioacetate group. We hypothesized that thioacetyl migration is prone to occur due to the labile thioacetate group even under weak basic conditions caused by the nucleophile, leading to this result. Therefore, we managed to inhibit the generation of thiol groups from thioacetate groups by the addition of an appropriate amount of conjugate acid/anhydride, successfully improving the synthesis of 4-thio-and 2,4-dithio-glycoside derivatives. The target products which were previously difficult to synthesize, were herein obtained in relatively high yields. Finally, 4-deoxy-and 2,4-dideoxy-glycoside derivatives were efficiently synthesized through the removal of thioacetate groups under UV light, starting from 4-thio-and 2,4-dithio-glycoside derivatives.

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“…25 Formation of the interglycosidic disulfide bond has also been achieved efficiently from the 1-S-acetyl form of glycosides via oxidation using iodine in combination with N-iodosuccinimide. 26 Furthermore, the copper(I)-catalysed oxidation of S-trityl-1thiomannosides directly produced the respective symmetrical mannosyl disulfide in good yields (around 70%). 27 It should be noted that the usefulness of m-chloroperoxybenzoic acid as an oxidant is far from ideal since it requires careful control of reaction conditions to avoid over-oxidation products, such as diglycosyl thiosulfinates and thiosulfonates, which are frequently obtained when it is utilised.…”

Section: Reviewmentioning

confidence: 99%