1206803-50-0Relevant articles and documents
Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system
Zhao, Yue-Tao,Niu, Shan,Huang, Lu-Bai,Wang, Ji-Ming,Yin, Zhao-Jun,Li, Qing,Li, Zhong-Jun
, p. 5022 - 5028 (2013/06/27)
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/Et 3SiH/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.
Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system
Yin, Zhao-Jun,Wang, Bo,Li, Yang-Bing,Meng, Xiang-Bao,Li, Zhong-Jun
supporting information; experimental part, p. 536 - 539 (2010/05/02)
[Chemical equation presented] A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers Into silyl ethers using Co2(CO)8-Et 3SIH under 1 atm of CO. The method was successfully used for the de-O-benzylatlon of perbenzylated monosaccharides with various anomerlc protecting groups, as well as natural disaccharldes and trisaccharides such as sucrose, raffinose, and melezltose In good yields (>80%).