Stereoselective Synthesis of 2-(β-C-Glycosyl)glycals: Access to Unusual β-C-Glycosides from 3-Deoxyglycals

被引：12
作者：
Reddy, Gadi Madhusudhan [1 ]
Rao, Boddu Uma Maheswara [1 ]
Sridhar, Perali Ramu [1 ]
机构：
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期
关键词：
HYDRIDE REDUCTIVE REARRANGEMENT; CONFORMATIONAL-ANALYSIS; GLYCALS; GLYCOSYLATION; STEREOCHEMISTRY; ISOMERIZATION; DISACCHARIDES; ROUTE;
D O I：
10.1021/acs.joc.5b02879
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the highly stereoselective synthesis of beta-(1 -> 2)-C-saccharides employing 3-deoxy- and 3-C-branched glycals as hermaphroditic substrates is revealed. The generality of the C-C bond formation reaction between the two sugar units is evaluated. The developed methodology is successfully applied to the synthesis of biologically significant subunits that are present in various natural products, which include mixed C-disaccharides with adjacent THP-THF rings, C-aryl glycosides, and highly functionalized beta-C-glycosides.
引用
收藏
页码：2782 / 2793
页数：12
相关论文
共 52 条
  • [31] Levy D.E., 2006, ORGANIC CHEM SUGARS
  • [32] Recent progress on the total synthesis of acetogenins from Annonaceae
    Li, Nianguang
    Shi, Zhihao
    Tang, Yuping
    Chen, Jianwei
    Li, Xiang
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2008, 4
  • [33] Identification of C-glycoside analogues that display a potent biological activity against murine and human invariant natural killer T cells
    Li, Xiangming
    Chen, Guangwu
    Garcia-Navarro, Raquel
    Franck, Richard W.
    Tsuji, Moriya
    [J]. IMMUNOLOGY, 2009, 127 (02) : 216 - 225
  • [34] Stereoselective C-glycosylation reactions of pyranoses:: The conformational preference and reactions of the mannosyl cation
    Lucero, CG
    Woerpel, KA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) : 2641 - 2647
  • [35] Maercker A, 2004, ORGANIC REACTIONS
  • [36] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS
    MARYANOFF, BE
    REITZ, AB
    [J]. CHEMICAL REVIEWS, 1989, 89 (04) : 863 - 927
  • [37] Synthesis of the C-linked disaccharide α-D-Man-(1→4)-D-Man employing a SmI2-Mediated C-glycosylation step:: En route to cyclic C-oligosaccharides
    Mikkelsen, LM
    Skrydstrup, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) : 2123 - 2128
  • [38] Nicotra F, 1997, TOP CURR CHEM, V187, P55
  • [39] Nishikawa T., 2008, GLYCOSCIENCE, P755
  • [40] Postema M.H. D., 1995, C GLYCOSIDE SYNTHESI
123456