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By Arefeva I.Ya.
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49 (i) PPh3, DEAD, BzOH; (ii) NaOMe, MeOH. 5 CARBONATES Alkyl carbonate derivatives greatly extend the versatility of acyl protection since the alkyl residue can be chosen to provide derivatives that are cleavable under highly speciﬁc conditions as tabulated below. Derivative Abbreviation Typical deprotection conditions Allyloxycarbonyl 2-(Trimethylsilylethyl)oxycarbonyl 9-Fluorenylmethyloxycarbonyl tert-Butyloxycarbonyl 2,2,2-Trichloroethyloxycarbonyl Benzyloxycarbonyl Alloc Pd(0) þ nucleophile Tmsec, Teoc F2 sources Fmoc Piperidine Boc TFA Troc Zn, AcOH Cbz, Z H2, Pd catalyst Although these derivatives offer great potential for highly site speciﬁc manipulations, their use in carbohydrate chemistry has been somewhat limited mainly because the procedures and strategies based on the classical protecting groups are tried and tested.
Bu4NI, 0 8C ! rt, 5 h. Notes. Alkylation under basic conditions (anionic benzylation). The tetrabutylammonium iodide catalyst enhances the reactivity of the alkylating agent by generating benzyl iodide in situ. The catalyst renders the use of a highly polar solvent such as DMF unnecessary, enabling a relatively non-polar solvent (THF) to be employed. Materials. 50 ml) ﬂammable, corrosive Ethyl acetate (150 ml þ chromatography solvent) highly ﬂammable, irritant Distilled water (150 ml) no risk Saturated solution of sodium hydrogen carbonate (150 ml) no risk Saturated solution of sodium chloride (100 ml) no risk Magnesium sulfate (drying agent) irritant, harmful by inhalation Petroleum ether (chromatography solvent) highly ﬂammable, harmful 36 2.
15 g, 75%). 44 (m, Ar-H, 10H); MS m/z (CI) 423 (M þ H, 21%), 265 (65), 205 (57), 105 (100). Method 4  Preparation of 2,3,4,6-tetra-O-benzyl-a-D -glucopyranosyl ﬂuoride. BnBr, Ag2O, rt, 4 h. Notes. Alkylation under essentially neutral conditions. The silver(I) oxide aids dissociation of bromide, enhancing the reactivity of the alkylating agent. Materials. 5 g, 114 mmol) irritant Methanol (10 ml) highly ﬂammable, toxic Celitew harmful by inhalation, possible irreversible effects Hexane (chromatography solvent) highly ﬂammable, harmful Diethyl ether (chromatography solvent) extremely ﬂammable, harmful Equipment.