Regioselective glycosylation:: Synthesis of α-indoline nucleosides

被引:9
|
作者
Brown, KL [1 ]
Chandra, T
Zou, S
Valente, EJ
机构
[1] Ohio Univ, Dept Chem & Biochem, Athens, OH 45701 USA
[2] Mississippi Coll, Dept Chem, Clinton, MS USA
关键词
coenzyme B-12; biosynthesis; regioselective; glycosylation;
D O I
10.1081/NCN-200067398
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.
引用
收藏
页码:1147 / 1165
页数:19
相关论文
共 50 条
  • [41] Zeolite-assisted regioselective synthesis of dinitronaphthalene
    Wang, Haocai
    Peng, Xinhua
    Shi, Chunjie
    Dong, Xiongzi
    Tai, Yanfang
    Liu, Hongtao
    RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (04) : 1495 - 1500
  • [42] Regioselective synthesis of novel N-aminotriazolophanes
    Chande, Madhukar S.
    Barve, Pravin A.
    Khanwelkar, Rahul R.
    Athalye, Shailesh S.
    Venkataraman, Deepak S.
    CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (01) : 21 - 28
  • [43] Synthesis of novel nucleosides and stereoselectivity of N-glycosidation
    Michigami, Kyosuke
    Uchida, Satoshi
    Adachi, Miho
    Hayashi, Masahiko
    TETRAHEDRON, 2013, 69 (02) : 595 - 599
  • [44] Synthesis and antimicrobial activity of 4-trifluoromethylpyridine nucleosides
    Alneyadi, Shaikha S.
    Abdulqader, Anas A.
    Salem, Alaa A.
    Abdou, Ibrahim M.
    HETEROCYCLIC COMMUNICATIONS, 2017, 23 (03) : 197 - 203
  • [45] Lipase-catalysed regioselective acylations in combination with regioselective glycosylations as a strategy for the synthesis of oligosaccharides: Synthesis of a series of fucosyllactose building blocks
    Rencurosi, A
    Poletti, L
    Russo, G
    Lay, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) : 1672 - 1680
  • [46] A GENERAL, REGIOSELECTIVE SYNTHESIS OF 2-ALKYLANILINES
    HARMATA, M
    KAHRAMAN, M
    SYNTHESIS-STUTTGART, 1994, (02): : 142 - 144
  • [47] Stannylene-Mediated Regioselective 6-O-Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides
    Maggi, Agnese
    Madsen, Robert
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (13) : 2683 - 2691
  • [48] From Stereocontrolled Glycosylation to Expeditious Oligosaccharide Synthesis
    Yasomanee, Jagodige P.
    Demchenko, Alexei, V
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 2013, 25 (141) : 13 - 42
  • [49] Total synthesis of eucryphin and its glycosylation derivatives
    Zhang, Yucheng
    Liu, Jiahao
    Xing, Hongxia
    Huang, Yaxuan
    Yao, Qian
    Kang, Tairan
    Guo, Xiaoqiang
    TETRAHEDRON, 2022, 122
  • [50] Recent Progress in the Synthesis and Glycosylation of Rare Sugars
    Wenninger, Marvin
    Poulsen, Martin L.
    Larsen, Megan E.
    Hauser, Nicole M.
    SYNTHESIS-STUTTGART, 2025, 57 (07): : 1265 - 1279