Glycosylation and Protecting Group Strategies Towards the Synthesis of Saponins and Bacterial Oligosaccharides: A Personal Account.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical record"
DOI: 10.1002/tcr.202000181
Abstract: Carbohydrates and their conjugates are not only involved in important biological processes but are also regarded as promising therapeutics and prophylactics. Over the last century, several glycosylation methodologies, glycosyl donors, and protecting groups have been… read more here.
Keywords: glycosylation protecting; protecting group; personal account; glycosylation ... See more keywords
Effects of lipophilicity, protecting group and stereochemistry on the antimalarial activity of carbohydrate-derived thiochromans
Sign Up to like & getrecommendations! Published in 2017 at "Medicinal Chemistry Research"
DOI: 10.1007/s00044-017-2105-5
Abstract: A series of novel carbohydrate-derived thiochromans has been successfully synthesized in order to investigate the influence of alkyl substituents on the aromatic ring of the thiophenol moiety in addition to the effect of protecting groups… read more here.
Keywords: carbohydrate derived; protecting group; antimalarial activity; derived thiochromans ... See more keywords
A novel use of catalytic zinc-hydroxyapatite columns for the selective deprotection of N-tert-butyloxycarbonyl (BOC) protecting group using flow chemistry
Sign Up to like & getrecommendations! Published in 2020 at "Journal of Flow Chemistry"
DOI: 10.1007/s41981-019-00052-x
Abstract: The development of a single step flow process for the deprotection of the common protecting group tert-butyloxycarbonyl (BOC) is presented. Conventional BOC deprotection methods can require up to 24 h to fully deprotect compounds and… read more here.
Keywords: butyloxycarbonyl boc; protecting group; chemistry; deprotection ... See more keywords
Investigation of protecting group for sialic acid carboxy moiety toward sialylglycopeptide synthesis by the TFA-labile protection strategy
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron"
DOI: 10.1016/j.tet.2021.132423
Abstract: Abstract The sialylation using sialyl donor with 2,6-dimethylbenzyl (DMBn) ester at C-1 carboxy group rapidly proceeded with good α-selectivity to yield sialyl-N-acetylgalactosaminylated 9-fluorenylmethoxycarbonyl (Fmoc) serine unit. The unit was used for the solid-phase peptide synthesis… read more here.
Keywords: tfa; protecting group; group; investigation protecting ... See more keywords
Utilization of the p-nitrobenzyloxycarbonyl (pNZ) amine protecting group and pentafluorophenyl (Pfp) esters for the solid phase synthesis of spiroligomers
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2018.05.041
Abstract: Abstract Spiroligomers are a class of peptidomimetics that connect interchangeable, stereochemically pure, cyclic monomers through pairs of amide bonds to form diketopiperazines between the monomers. This enables them to adopt predictable and programmable structure due… read more here.
Keywords: phase synthesis; nitrobenzyloxycarbonyl pnz; protecting group; solid phase ... See more keywords
Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides†.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c01652
Abstract: The 5S, 8'R, and 10'R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1' emerged from syntheses of… read more here.
Keywords: labile protecting; militarinone; acid labile; protecting group ... See more keywords
Highly Chemoselective Ni-Catalyzed Protecting-Group-Free 2,2'-Biphenol Synthesis and Mechanistic Insights.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01367
Abstract: The utilization of readily available starting materials to produce useful molecules is often challenged by selectivity issues. In this study, a Ni-catalyzed protecting-group-free C-C coupling protocol is described for the efficient synthesis of 2,2'-biphenol derivatives.… read more here.
Keywords: catalyzed protecting; biphenol; group free; synthesis ... See more keywords
Synthesis of Deoxyaspidodispermine Based on a Functional Protecting Group Strategy.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c01878
Abstract: A synthesis of deoxyaspidodispermine was produced from homotyramine. This approach is based on the application of a functional protecting group strategy that not only masks the reactivity of sensitive groups during crucial steps but also… read more here.
Keywords: functional protecting; group; synthesis deoxyaspidodispermine; group strategy ... See more keywords
Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b03321
Abstract: The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation.… read more here.
Keywords: participation; dual participation; protecting group; group ... See more keywords
Functionalization of Tetrazoles Bearing the Electrochemically Cleavable 1N-(6-Methylpyridyl-2-methyl) Protecting Group
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DOI: 10.1021/acsomega.2c01633
Abstract: 6-Methylpyridyl-2-methyl protected tetrazoles can be C–H deprotonated using the turbo-Grignard reagent and involved in the reactions with aldehydes and ketones. The protecting group can be cleaved under reductive electrochemical conditions using Pb bronze as a… read more here.
Keywords: protecting group; methylpyridyl methyl; functionalization tetrazoles;
Innovation in protecting-group-free natural product synthesis
Sign Up to like & getrecommendations! Published in 2019 at "Nature Reviews Chemistry"
DOI: 10.1038/s41570-018-0071-1
Abstract: Many natural products have intriguing medicinal properties that arise from their fascinating chemical structures. This structural complexity means that the total synthesis of natural products often requires the use of protecting-group chemistry, an approach that… read more here.
Keywords: natural products; protecting group; chemistry; synthesis ... See more keywords