Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 8, Pages 4164-4175Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00140
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Funding
- National Science Funding of China [21272220]
- State Key Laboratory of Drug Research [SIMM1403KF-12]
- NSFC-Shandong Joint Fund [U1406402]
- Project on Scientific development in Shangdong Province [2012GHY11526]
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A mild and convenient protocol for direct synthesis of beta-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 degrees C to room temperature and afforded the corresponding beta-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.
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