Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: Reduction of the azide group with Ph(3)P-H(2)O to amino functionality followed by coupling with amino acids leads to the synthesis of novel 2-deoxy-beta-N-glycopeptides irrespective of the geometry of initial azido sugars.
Abstract: A novel reagent system comprising Me 3 SiN 3 and 20 mol % of Me 3 SiONO 2 permits conversion of glycals to 1-azido 2-deoxy sugars in one step in fair to good yields. Galactals offer higher stereoselectivities than do the glucals. Reduction of the azide group with Ph 3 P-H 2 O to amino functionality followed by coupling with amino acids leads to the synthesis of novel 2-deoxy-β-N-glycopeptides irrespective of the geometry of initial azido sugars. Using this protocol, a new γ-sugar amino acid derivative is also procured.
41 citations
TL;DR: The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups.
Abstract: The total synthesis of the potent cytotoxin theopederin D has been achieved through the use of an oxidative carbon–carbon bond cleavage reaction to form an acyliminium ion in the presence of acid labile acetal groups Other key transformations include an acid mediated functionalization of a tetrahydrofuranyl alcohol in the presence of a tetrahydropyranyl alcohol, a syn-selective glycal epoxide opening, and a catalytic asymmetric aldehyde-acid chloride condensation.
40 citations
TL;DR: In this article, the synthesis of anthracycline C-glycoside constitutes a key development in a synthetic program directed toward synthesis of Cglycosides of the benzo [d] naphtho [1,2-b] pyran-6-one series related to the ravidomycin, gilvocarcin, chrysomycin class of antibiotics.
40 citations
TL;DR: In this article, a stereoselective synthesis of methyl 3-azido 2,3,6-trideoxy-α-L-arabino-hexopyranoside from di-O-acetyl L-rhamnal is reported.
Abstract: A stereoselective synthesis of methyl (or benzyl) 3-azido-2,3,6-trideoxy-α-L-arabino-hexopyranoside from di-O-acetyl-L-rhamnal is reported; it proceeds via addition of hydrazoic acid to a hex-2-enopyranose, followed by acetylation and glycosidation with the appropriate alcohol, in the presence of K-10 montmorillonite as catalyst.
39 citations
TL;DR: In this paper, a 3-O-benzyl-1-(tri-n-butylstannyl)furanoid glycal was derived from the 1-phenylsulfonyl glycal using AIBN.
39 citations