By Amelia Pilar Rauter, Thisbe Lindhorst, Anne Imberty, Jesus Jimenez-Barbero, Ana M. Gomez, Ramon J Estevez, Jose A.S. Cavaleiro, Slawomir Jarosz, Vladimir Kren, J. Cristobal Lopez, Francesso Nicotra, Yves Queneau, Immaculada Robina, Patrick Rollin, Pierre
Carbohydrate Chemistry offers evaluation assurance of all courses correct to the chemistry of monosaccharides and oligosaccharides in a given yr. the volume of study during this box showing within the natural chemical literature is expanding a result of improved value of the topic, specifically in components of medicinal chemistry and biology. In no a part of the sphere is that this extra obvious than within the synthesis of oligosaccharides required via scientists operating in glycobiology. Clycomedicinal chemistry and its reliance on carbohydrate synthesis is now rather well tested, for instance, through the practise of particular carbohydrate- dependent antigens, particularly cancer-specific oligosaccharides and glycoconjugates. insurance of themes resembling nucleosides, amino-sugars, alditols and cyclitols additionally covers a lot study of relevance to organic and medicinal chemistry. each one quantity of the sequence brings jointly references to all released paintings in given parts of the topic and serves as a entire database for the energetic examine chemist professional Periodical experiences offer systematic and certain evaluate assurance in significant parts of chemical study. Compiled by means of groups of best gurus within the correct topic parts, the sequence creates a distinct provider for the lively learn chemist, with ordinary, in-depth debts of development particularly fields of chemistry. topic assurance inside assorted volumes of a given name is the same and book is on an annual or biennial foundation.
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Additional info for Carbohydrate Chemistry: Volume 35 (Specialist Periodical Reports)
Yamasaki, Y. Hohno, R. Ohtaki, K. Ueda, H. Suezawa, Y. Umezawa and M. Nishio, Carbohydr. , 2007, 342, 1202. 13 I. Tvaroska and T. Bleha, Adv. Carbohydr. Chem. , 1989, 47, 45; I. Tvaroska and J. P. Carver, J. Phys. , 1995, 99, 6234. 14 E. Juaristi and G. Cuevas, Tetrahedron, 1992, 48, 5019. 15 H. Booth, J. M. Dixon and S. A. Readshaw, Tetrahedron, 1992, 48, 6151. 16 For conformational comparisons between O- and C-glycosyl compounds, see: J. Jimenez-Barbero, J. F. Espinosa, J. L. Asensio, F. Can˜ada and A.
Structural elements of the reactants and a careful choice of reaction conditions give good 1,2-cis stereoselectivities. 21 Scheme 1 Glycosylation mechanisms. The participation of solvents plays an important role. The use of non-polar solvents, favours the glycosylation reaction to follow a SN2-like 36 | Carbohydr. , 2009, 35, 33–70 This journal is c The Royal Society of Chemistry 2009 pathway. Under SN1-type conditions, the participation of solvents can markedly improve the stereoselectivity in glycosylation of donors with non-assisting functionalities.
Subsequent displacement of the equatorial anomeric sulfonium ion by a sugar alcohol leads to the formation of the 1,2-cis-glycoside (Scheme 4(A), pathway b). Scheme 4 (A) Neighbouring group participation by an (S)-auxiliary at C-2 leading to 1,2-cis-glycosides. (B) Neighbouring group participation by an (R)-auxiliary at C-2 leading to 1,2-trans-glycosides. Alternatively, the use of an auxiliary with an (R)-stereochemistry at the phenyl-2-(phenylsulfanyl)ethyl moiety will lead to the formation of a 1,2-trans-glycoside because in this case the trans-decalin system will exert unfavourable steric interactions.