Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system

A convenient approach for synthesis of raffinose, stachyose, and verbascose using sucrose as the starting material is presented. The key step is the regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system, followed by a high α-selective glycosylation. The newly developed de-O-benzylation system is efficient in removing the primary benzyl groups of sucrose and raffinose under mild condition and with high selectivity. Using thioglycoside as donor, NIS/AgOTf as promoter and DTBMP as additive, glycosylation of acid labile sucrose substrate is achieved in high yield.

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