期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 10, 页码 5189-5195出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00601
关键词
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'The beta-selective phenylation of benzyl and boronate protected 1,6-anhydroglucose and the direct phenylation of unprotected 1,6-anhydroglucose (10), pretreated with i-Bu2AlH, i-Bu3Al, Et3Al, Me3Al, or n-octyl(3)Al, with triphenylalane or aryl(chloro)alanes is reported. The utility of the unprotected version of the method is demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin (1a), from commercially available 10 in one C-C bond-forming step. This approach circumvents the need for conventional protecting groups, and therefore no formal protection and deprotection steps are required.
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