81972-20-5Relevant academic research and scientific papers
Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation
Bennett, Clay S.,Ling, Jesse
, p. 4304 - 4308 (2020/02/11)
C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results i
A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids
Paterson, Duncan E.,Griffin, Frank K.,Alcaraz, Marie-Lyne,Taylor, Richard J. K.
, p. 1323 - 1336 (2007/10/03)
Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Synthesis of C-linked glycopyranosyl serines via a chiral glycine enolate equivalent.
Nolen, Ernest G,Watts, Micah M,Fowler, Daniel J
, p. 3963 - 3965 (2007/10/03)
[formula: see text] The stereoselective preparation of C-linked D-gluco- and D-galactopyranosyl L-serines in their alpha and beta forms is herein reported. The syntheses require the conversion of the allyl C-glycopyranosides into their iodoethyl derivativ
A general strategy for the convergent synthesis of fused polycyclic ethers via B-alkyl Suzuki coupling: Synthesis of the ABCD ring fragment of ciguatoxins
Sasaki, Makoto,Ishikawa, Makoto,Fuwa, Haruhiko,Tachibana, Kazuo
, p. 1889 - 1911 (2007/10/03)
A new method for convergent coupling of fused polycyclic ethers has been developed, which relies on B-alkyl Suzuki crosscoupling of lactone-derived enol triflates or phosphates. The strategy was successfully applied to a convergent synthesis of the ABCD r
Ramberg - Backlund approaches to the synthesis of C-linked disaccharides
Griffin, Frank K.,Paterson, Duncan E.,Taylor, Richard J. K.
, p. 2939 - 2942 (2007/10/03)
Readily available S-glycoside dioxides were utilized in a Ramberg- Backlund rearrangement for the construction of C-linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated
A general method for convergent synthesis of polycyclic ethers based on Suzuki cross-coupling: Concise synthesis of the ABCD ring system of ciguatoxin
Sasaki, Makoto,Fuwa, Haruhiko,Ishikawa, Makoto,Tachibana, Kazuo
, p. 1075 - 1077 (2008/02/09)
(matrix presented) A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupli
Preferred Conformation of C-Glycosides. 7. Preferred Conformation of Carbon Analogues of Isomaltose and Gentiobiose
Goekjian, Peter G.,Wu, Tse-Chong,Kang, Han-Young,Kishi, Yoshito
, p. 6422 - 6434 (2007/10/02)
The preferred solution conformation of the 1,6-linked C-disaccharides 3 and 4, carbon analogues of methyl isomaltoside and methyl gentiobioside, was shown to be 3-A and 4-A, respectively, by 1H NMR spectroscopy.
Epimerization of α- to β-C-Glucopyranosides under Mild Basic Conditions
Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio
, p. 1275 - 1280 (2007/10/02)
A number of β-C-glucopyranosides having an activated methylene or methine group bonded to the anomeric carbon are obtainable in quantitative yield from the corresponding α-isomers by simple equilibration catalysed by various bases at room temperature.
