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Effective Synthesis of alpha-D-GlcN-(1 -> 4)-D-GlcA/L-IdoA Glycosidic Linkage under Gold(I) Catalysis
Alternative Title一价金催化的alpha-d-GlcN-(1->4)-d-GlcA/l-IdoA糖苷键合成
Li JK(李家昆)1; Dai YW(代元伟)1; Li W(李微)1; LAVAL STEPHANE1; Xu P(徐鹏)1; Yu B(俞飚)1
2015
Source PublicationAsian J. Org. Chem.
Volume4Issue:8Pages:756-762
AbstractAn effective glycosylation procedure for the stereoselective construction of the alpha-D-GlcN-(1-->4)-D-GlcA/L-IdoA glycosidic linkage found in heparin and heparan sulfate is reported. The condensation occurs between 2-deoxy-2-azido-D-glucopyranosyl (D-GlcN) ortho-hexynylbenzoate donors and uronate acceptors (D-GlcA/L-IdoA) under mild gold(I)-catalyzed conditions. Optimal results are obtained when performing the reaction in CH2Cl2, from -72 degrees C to room temperature in the presence of 4 angstrom molecular sieves and under the promotion of [Ph3PAuCl]/AgOTf or [(1,1-bis-(diphenylphosphino)methane)(AuCl)(2)]/AgOTf as a source of the gold(I) catalyst. A donor/acceptor ratio of 3:1 as well as a loading of 0.6 equivalents of the gold(I) catalyst are essential to attain high yields and selectivity, particularly for the [1+1] and [1+2] glycosylations.
Subtype论文
Subject Area生命有机化学
DOI10.1002/ajoc.201500113
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000359426800009
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39520
Collection生命有机化学国家重点实验室
Corresponding AuthorYu B(俞飚)
Affiliation1.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
2.中国科学技术大学
Recommended Citation
GB/T 7714
Li JK,Dai YW,Li W,et al. Effective Synthesis of alpha-D-GlcN-(1 -> 4)-D-GlcA/L-IdoA Glycosidic Linkage under Gold(I) Catalysis[J]. Asian J. Org. Chem.,2015,4(8):756-762.
APA 李家昆,代元伟,李微,LAVAL STEPHANE,徐鹏,&俞飚.(2015).Effective Synthesis of alpha-D-GlcN-(1 -> 4)-D-GlcA/L-IdoA Glycosidic Linkage under Gold(I) Catalysis.Asian J. Org. Chem.,4(8),756-762.
MLA 李家昆,et al."Effective Synthesis of alpha-D-GlcN-(1 -> 4)-D-GlcA/L-IdoA Glycosidic Linkage under Gold(I) Catalysis".Asian J. Org. Chem. 4.8(2015):756-762.
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