期刊
ORGANIC LETTERS
卷 -, 期 -, 页码 -出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03256
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资金
- Guangdong Basic and Applied Basic Research Foundation [2021A1515010189, 2022A1515011109]
- Fundamental Research Funds for the Central Universities [22lglj10]
- Shenzhen Science and Technology Program from China [GXWD20201231165807008, 20200825175848001]
- Japan Society for the Promotion of Science [18K05345, 19H00929]
A versatile ZnI2-directed fi-galactosylation approach using a 4,6-O-tethered and 2-O-Bn galactosyl donor is reported for the stereoselective and efficient synthesis of fi-O-galactosides. The reaction tolerates a wide range of functional groups and complex molecular architectures, providing stereocontrolled fi-galactosides in moderate to excellent yields. The practicality of this transformation is demonstrated through the synthesis of a tetrasaccharide arabinogalactan fragment with high stereoselectivity.
Conventional glycosylation with galactosyl donors having C-2 benzyl (Bn) ether-type functionality often leads to anomeric mixtures, due to the anomeric and steric effects that stabilize the 1,2-cis-a- and 1,2-trans-fi-glycosides, respectively. Herein we report a versatile ZnI2-directed fi-galactosylation approach employing a 4,6-O-tethered and 2-O-Bn galactosyl donor for the stereoselective and efficient synthesis of fi-O-galactosides. With a broad substrate scope, the reaction tolerates a wide range of functional groups and complex molecular architectures, providing stereocontrolled fi-galactosides in moderate to excellent yields. The practicality of this transformation is demonstrated through the synthesis of a tetrasaccharide arabinogalactan fragment with high stereoselectivity.
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