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Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates
Alternative Title1-alpha-glycosyloxy-isochromenylium-4-gold(I)中间体介导的高立体选择性的beta-甘露糖糖苷化
Zhu YG(朱玉根); Yu B(俞飚)
Source PublicationChem.-Eur. J.
AbstractWhile the gold(I)-catalyzed glycosylation reaction with 4,6-O-benzylidene tethered mannosyl ortho-alkynylbenzoates as donors falls squarely into the category of the Crich-type -selective mannosylation when Ph3PAuOTf is used as the catalyst, in that the mannosyl -triflates are invoked, replacement of the -OTf in the gold(I) complex with less nucleophilic counter anions (i.e., -NTf2, -SbF6, -BF4, and (-BAr4F)) leads to complete loss of -selectivity with the mannosyl ortho-alkynylbenzoate -donors. Nevertheless, with the -donors, the mannosylation reactions under the catalysis of Ph3PAuBAr4F (BAr4F=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) are especially highly -selective and accommodate a broad scope of substrates; these include glycosylation with mannosyl donors installed with a bulky TBS group at O3, donors bearing 4,6-di-O-benzoyl groups, and acceptors known as sterically unmatched or hindered. For the ortho-alkynylbenzoate -donors, an anomerization and glycosylation sequence can also ensure the highly -selective mannosylation. The 1--mannosyloxy-isochromenylium-4-gold(I) complex (C), readily generated upon activation of the -mannosyl ortho-alkynylbenzoate (1) with Ph3PAuBAr4F at -35 degrees C, was well characterized by NMR spectroscopy; the occurrence of this species accounts for the high -selectivity in the present mannosylation.
Subject Area生命有机化学
Indexed BySCI
WOS IDWOS:000355287000020
Citation statistics
Cited Times:49[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorYu B(俞飚)
Affiliation中科院上海有机化学研究所, 生命有机化学国家重点实验室
Recommended Citation
GB/T 7714
Zhu YG,Yu B. Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates[J]. Chem.-Eur. J.,2015,21(24):8771-8780.
APA 朱玉根,&俞飚.(2015).Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates.Chem.-Eur. J.,21(24),8771-8780.
MLA 朱玉根,et al."Highly Stereoselective -Mannopyranosylation via the 1--Glycosyloxy-isochromenylium-4-gold(I) Intermediates".Chem.-Eur. J. 21.24(2015):8771-8780.
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