By Marco Brito Arias
From the reviews:
"Brito-Arias … offers an summary of the buildings and artificial arrangements of O-, N-, and C-glycosides, in addition to dialogue of the conformational positive aspects and organic functionality of chosen examples. … The association of the booklet offers a prepared source for researchers looking details. certainly, the references to released artificial technique or analytical info integrated on the finish of every bankruptcy can be helpful for researchers looking more information or information on a particular subject. … Summing Up: urged. Graduate scholars via professionals." (P. W. Baures, selection, Vol. forty four (11), July, 2007)
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Extra resources for Synthesis and Characterization of Glycosides
Sample text
Vi) a) TFA/CHCl3. b) FmocCl/iPrNEt/CH2Cl2-MeOH, 69% (two steps). c) Jones oxidation/acetone, 77%. 29. Synthesis of C-glycoside serine analogue by Ramberg-B¨acklung rearrangement. 3 Enzymatic Synthesis The enzymatic synthesis of monosaccharides and carbohydrates mimetics by enzyme catalysts is performed mainly by a group of lyases known as aldolases. This O R1 R2 OH i,ii O R1 NHCbz R1 = OAc, R2 = H R1 = H , R2 = OAc R2 OUDP NHCbz α/β 1:2 i) TMS-Cl, TMS-I, –78oC. ii) UDP, Bu4N salt, 60%. 30. Synthesis of protected UDP epi-vancosamine.
8 The Leaving Groups As mentioned above, the anomeric hydroxyl group can be replaced under suitable conditions with a good leaving group. Initially, the use of halogens such as fluorine, chlorine, and bromine was the strategy of choice, and particulary the last since it presents the best balance between reactivity and stability and this is why it has been extensively used for preparing glycosides. However, halides are in most cases labile and undergo decomposition. Consequently a number of other leaving groups have been designed for glycoside chemistry, and among them, imidates, sulfur, sulfonates, silyl groups, phoshates, and acetates are equally important alternatives.
17 A method reported for the preparation of C-glycosyl alanines involves the use of (R)-methyleneoxazolidinone, which was linked to the peracetylated iodosugars under promoted radical additions. 18 C-analogues of glycosyl serines have been prepared by a number of methods and among them Strecker, Witting, and Sharpless asymmetric aminohydroxylation reactions19 . One of them describes their synthesis via coupling of anomeric pyridyl sulfone with an electrophiles center under samarium catalysis. 3:1).
