2011
DOI: 10.1021/cr100444b
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2-Oxoglycosyl (“Ulosyl”) and 2-Oximinoglycosyl Bromides: Versatile Donors for the Expedient Assembly of Oligosaccharides with β-d-Mannose, β-l-Rhamnose, N-Acetyl-β-d-mannosamine, and N-Acetyl-β-d-mannosaminuronic Acid Units

Abstract: |Chem. Rev. 2011, 111, 5569-5609 Chemical Reviews REVIEW in 1900, 16 their 2-oxohexosyl ("ulosyl") analogues were not encountered until 73 years later, when Collins et al. 17 subjected the 2-O-unprotected hexosyl chlorides of D-glucose and D-galactose to a ruthenium tetroxide oxidation, e.g., 1 f 2 (Scheme 2). The somewhat intricate accessibility of 2 and its galacto analoguefive steps from the underlying sugar in modest overall yields (15À20%)-and their capricious obtention as gums, however, have not invit… Show more

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Cited by 33 publications
(23 citation statements)
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“…The proteolytic cleavage of APP is initiated non-amyloidogenically by α-secretase. ADAM10 and ADAM17 are two main enzymes with α-secretase activity [ 118 - 120 ]. Although ADAM10 is necessary for APP α-secretase cleavage, ADAM17 may also be involved, although it is not crucial [ 121 ].…”
Section: Discussionmentioning
confidence: 99%
“…The proteolytic cleavage of APP is initiated non-amyloidogenically by α-secretase. ADAM10 and ADAM17 are two main enzymes with α-secretase activity [ 118 - 120 ]. Although ADAM10 is necessary for APP α-secretase cleavage, ADAM17 may also be involved, although it is not crucial [ 121 ].…”
Section: Discussionmentioning
confidence: 99%
“…For example, (i) 3,4,6‐tri‐ O ‐benzyl d ‐glycals can act as glycosyl donors and thus could be used in the synthesis of oligosaccharides and other enantiomerically pure organic molecules, (ii) a variety of nucleophiles can be introduced at C‐1 position of a glycal through S N 1′ reaction which possess a good leaving group at C‐3 carbon with migration of the double bond in a reaction called the Ferrier reaction . (iii) glycals allow a variety of functionalizations at C‐2 to lead to highly useful synthons such as 2‐nitro‐, 2‐halo, 2‐formyl, 2‐sulfonyl‐, and 2‐acetoxy glycals . These synthons have been widely used in the synthesis of biologically active compounds like iminosugars, C‐, O ‐, and N ‐glycosides, and N ‐glycopeptides .…”
Section: Introductionmentioning
confidence: 99%
“…On the other hand, the present work describes a first report of a one‐step synthesis toward 1,2‐dihydrobenzofuran‐fused C ‐aryl glycosides and C2‐ O ‐phenolic glycals from 1,2‐anhydrosugars. The latter products resemble 2‐acetoxyglycals, which have been well utilized in carbohydrate chemistry by Lichtenthaler and thus could serve as a new class of synthons in synthetic chemistry.…”
Section: Resultsmentioning
confidence: 99%