By Bessi U.
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Extra info for An analytic counterexample to the KAM theorem
Anomeric effect on halogens. 9. 9 Glycosyl Donors This term is used to deﬁne a glycosidic moiety that contains a leaving group at the anomeric position. When a glycosyl donor is reacted in the presence of a catalyst (also known as promoter) with a free alcohol called glycosyl acceptor, it will produce an O-glycosidic linkage. The ﬁrst glycosyl donors developed and used speciﬁcally for glycoside formation were the glycoyl halides. As mentioned above, glycosyl bromide and chloride are the most widely used halides, and are the glycosyl donors used for the preparation of O-glycosides according to the methods reported by Michael, Koenigs-Knorr and Helferich (see O-glycoside formation).
45. Azido methods for the preparation of aminosacharides. 6. Synthesis of Carbohydrates Mimetics OBn OBn OBn OBn O i O 33 OR AcO AcO N3 R= NO2 ii R=H i) CAN, NaN3, CH3CN, –15oC, 45%. PhSH, DIEA, 91%. t. ii) NaN3, DMF ref 1 OBn N3 i, ii O HO BnO OBn O BnO OBn OMe OBn OMe i) Tf2O, Py/ CH2Cl2. 45. (continued) OR 34 1. Glycosides, Synthesis, and Characterization OEt O SH i EtO O ii OH HO HO HO S OH OH iii OH AcO S AcO AcO SH HO H O OH iv OH OAc OH AcO AcO AcO S OAc i) a) AcSK, AcSH. b) HCl. ii) a) DHAP FDP A.
The fusion method consists of the reaction between the glycosyl acetate as glycosyl donor with the glycosyl acceptor in the presence of a Lewis acid as a promoter to generate the corresponding glycoside. 63 and to imidates, the latter by a two-step process. The ﬁrst step involves the removal of the anomeric acetate with base, among them hydrazine, benzylamine, ammonia, and piperidine, which are the most preferred. The resulting hydroxyl group is obtained as a mixture of anomers and is subsequently used for the preparation of the glycosyl imidate (see Imidate CO2Me O Me3CCO2 Me3CCO2 CO2Me R-OH i Me3CCO2 Me3CCO2 Me3CCO2 Me3CCO2 I i) NIS/I2, then TMSOTf.