Protecting Groups 2018
DOI: 10.1002/9783527697014.ch3
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Protecting Groups at the Secondary Positions of Carbohydrates

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Cited by 7 publications
(6 citation statements)
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“…Beyond the concept of ester migration during participation, it is commonly known that acyl groups in organic molecules are prone to intramolecular migration between the hydroxy groups, as first demonstrated for carbohydrates by Fischer in 1920 . Several studies providing closer insights into the actual migration process have been performed since, mostly in monosaccharide derivatives, although also larger carbohydrate molecules have been addressed, albeit less frequently. The often spontaneous migration, particularly under basic conditions, significantly hampers the use of partially acylated carbohydrate derivatives in synthesis and must always be considered in all isolation, characterization and identification processes of both synthetic compounds and natural products. ,− …”
Section: Introductionmentioning
confidence: 99%
“…Beyond the concept of ester migration during participation, it is commonly known that acyl groups in organic molecules are prone to intramolecular migration between the hydroxy groups, as first demonstrated for carbohydrates by Fischer in 1920 . Several studies providing closer insights into the actual migration process have been performed since, mostly in monosaccharide derivatives, although also larger carbohydrate molecules have been addressed, albeit less frequently. The often spontaneous migration, particularly under basic conditions, significantly hampers the use of partially acylated carbohydrate derivatives in synthesis and must always be considered in all isolation, characterization and identification processes of both synthetic compounds and natural products. ,− …”
Section: Introductionmentioning
confidence: 99%
“…Another benzyl ether in the form of Nap ethers gained momentum as their deprotection conditions are orthogonal to the benzyl ethers . In view of this, alcohol 7 was treated with Nap carbonate 30 in the presence of catalytic quantities of Au phosphite ( 2 ) and AgOTf in CH 2 Cl 2 to note the formation of Nap ether 31 in 62% yield.…”
Section: Results and Discussionmentioning
confidence: 99%
“…4). 120 Selecting the best nitrogen protecting group for a particular target involves often trial and error experimentation (see Section 6.4, Scheme 3). 115,117,121–124…”
Section: Glycan Connectivitymentioning
confidence: 99%