- General synthesis of C-glycosyl amino acids via proline-catalyzed direct electrophilic α-amination of C-glycosylalkyl aldehydes
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(Chemical Equation Presented) Non-natural axially and equatorially linked C-glycosyl α-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R α-configuration were prepared by D- and L-proline-catalyzed (de >95%) α-aminati
- Nuzzi, Andrea,Massi, Alessandro,Dondoni, Alessandro
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supporting information; experimental part
p. 4485 - 4488
(2009/05/27)
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- A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids
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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.
- Paterson, Duncan E.,Griffin, Frank K.,Alcaraz, Marie-Lyne,Taylor, Richard J. K.
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p. 1323 - 1336
(2007/10/03)
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- exo-Glycal approaches to C-linked glycosyl amino acid synthesis
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Two novel routes to C-linked glycosyl amino acids are described; the first involves elaboration of an exo-glycal and subsequent Ramberg-Backlund rearrangement of a sulfone intermediate to give, after functional group manipulation, a protected C-glycosyl serine, while the second uses hydroboration-Suzuki coupling of the same exo-glycal to produce ultimately the corresponding C-glycosyl asparagine analogue.
- Campbell, Andrew D.,Paterson, Duncan E.,Raynham, Tony M.,Taylor, Richard J.K.
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p. 1599 - 1600
(2007/10/03)
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- Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O- glycosyl serine and N-glycosyl asparagine
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A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the α-amino acid side chain at the anomeric carbon of sugars. This new functio
- Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
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p. 933 - 944
(2007/10/03)
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