Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation

被引:4
|
作者
Wang, Tinghua [1 ]
Singh, Yashapal [1 ]
Stine, Keith J. [1 ]
Demchenko, Alexei V. [1 ]
机构
[1] Univ Missouri, Dept Chem & Biochem, One Univ Blvd, St Louis, MO 63121 USA
基金
美国国家科学基金会;
关键词
Glycosylation; Nitrate; Oligosaccharides; Carbohydrates; GLYCAN BIOMARKERS; ACTIVATION; LANTHANIDE(III); IDENTIFICATION; PLATFORM; DONORS;
D O I
10.1002/ejoc.201801272
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.
引用
收藏
页码:6699 / 6705
页数:7
相关论文
共 50 条
  • [21] Synthesis of Fluorinated Glycosyl Amino Acid Building Blocks for MUC1 Cancer Vaccine Candidates by Microreactor-Assisted Glycosylation
    Oberbillig, Thomas
    Loewe, Holger
    Hoffmann-Roeder, Anja
    JOURNAL OF FLOW CHEMISTRY, 2012, 2 (03) : 83 - 86
  • [22] Synthesis of glycosyl phosphates from acetylated glycosyl nitrates
    Illarionov, PA
    Torgov, VI
    Hancock, IC
    Shibaev, VN
    Illarionova, PA
    TETRAHEDRON LETTERS, 1999, 40 (22) : 4247 - 4250
  • [23] Chemical building blocks for the biorefinery
    Werpy, TA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U1694 - U1694
  • [24] Nanocrystals as chemical building blocks
    Coelfen, Helmut
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [25] Glycosylation based on glycosyl phosphates as glycosyl donors
    Vankayalapati, H
    Jiang, SD
    Singh, G
    SYNLETT, 2002, (01) : 16 - 25
  • [26] GLYCOSYLATION USING GLYCOSYL PHOSPHITE AS A GLYCOSYL DONOR
    WATANABE, Y
    NAKAMOTO, C
    YAMAMOTO, T
    OZAKI, S
    TETRAHEDRON, 1994, 50 (22) : 6523 - 6536
  • [27] Glycosyl fluoride - A superb glycosyl donor in glycosylation
    Mukaiyama, T
    Jona, H
    PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2002, 78 (04): : 73 - 83
  • [28] OLIGOSACCHARIDES AS BUILDING-BLOCKS FOR GLYCOSYL CHAIN CONSTRUCTION - THEIR PREPARATION AND UTILIZATION
    KUZUHARA, H
    SAKAIRI, N
    TAKAHASHI, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1992, 50 (05) : 391 - 400
  • [29] Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates
    Ziegler, T
    Röseling, D
    Subramanian, LR
    TETRAHEDRON-ASYMMETRY, 2002, 13 (09) : 911 - 914
  • [30] O-Benzoxazolyl imidates as versatile glycosyl donors for chemical glycosylation
    Nigudkar, Swati S.
    Parameswar, Archana R.
    Pornsuriyasak, Papapida
    Stine, Keith J.
    Demchenko, Alexei V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (24) : 4068 - 4076