Synthesis of 2,3-diazido-2,3-dideoxy-β-D-mannosides and 2,3-diazido-2,3-dideoxy-β-D-mannuronic acid via stereoselective anomeric O-alkylation

被引：0
|
作者：
Banjara, Rama [1 ,2 ]
Thapa, Prakash [1 ,2 ]
Kela, Shailja Hitesh [1 ,2 ]
Wu, Fenglang [1 ,2 ]
Zhu, Jianglong [1 ,2 ]
机构：
[1] Univ Toledo, Dept Chem & Biochem, 2801 West Bancroft St, Toledo, OH 43606 USA
[2] Univ Toledo, Sch Green Chem & Engn, 2801 West Bancroft St, Toledo, OH 43606 USA
来源：
CARBOHYDRATE RESEARCH | 2024年 / 545卷
基金：
美国国家卫生研究院;
关键词：
Anomeric O -alkylation; beta-Mannoside; beta-Mannuronic acid; Bacterial polysaccharides; TRISACCHARIDE REPEATING-UNIT; CONTAINING GLYCAN CHAIN; POLYSACCHARIDE;
D O I：
10.1016/j.carres.2024.109279
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：
Stereoselective synthesis of 2,3-diazido-2,3-dideoxy-beta-d-mannosides has been accomplished via Cs2CO3-mediated anomeric O-alkylation of 2,3-diazido-2,3-dideoxy-beta-d-mannoses with primary electrophiles. Selective oxidation of the C6 primary alcohol of the 2,3-diazido-2,3-dideoxy-beta-d-mannoside successfully produced corresponding 2,3-diazido-2,3-dideoxy-beta-d-mannuronic acid.
引用
收藏
页数：7
相关论文
共 50 条
  • [21] SYNTHETIC NUCLEOSIDES .68. STUDIES ON SYNTHESIS OF CIS-2,3-DIAMINO SUGARS .8. DERIVATIVES OF 2,3-DIAMINO-2,3-DIDEOXY-D-RIBOSE AND 2,3-DIDEOXY-2,3-IMINO-D-RIBOSE
    BAKER, BR
    HULLAR, TL
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12): : 4053 - &
  • [22] SYNTHESIS OF 2,3-(CARBOXYMETHYLENE)- AND 2,3-(2-HYDROXYETHYLIDENE)-2,3-DIDEOXY-D-MANNOSE - MONOSACCHARIDES WITH A CYCLOPROPANE RING
    MEYERZUR.W
    KAMPRATH.U
    CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (02): : 673 - &
  • [23] SYNTHESIS OF 2,3-DIAMINO-2,3-DIDEOXY-D-MANNOSE DERIVATIVES VIA AZIDO-SUGAR INTERMEDIATES
    GUTHRIE, RD
    MURPHY, D
    CHEMISTRY & INDUSTRY, 1962, (32) : 1473 - 1473
  • [24] Synthesis of 9-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)adenine
    Sivets, Grigorii G.
    Kalinichenko, Elena N.
    Mikhailopulo, Igor A.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12): : 1387 - 1389
  • [25] SYNTHESIS OF 1-(2,3-DIDEOXY-2,3-DIFLUORO-BETA-D-LYXOFURANOSYL)CYTOSINE
    JEONG, LS
    MARQUEZ, VE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 66 - MEDI
  • [26] Prop-2-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
    Mesfin, Fanuel M.
    Kinfe, Henok H.
    Muller, Alfred
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3308 - U1865
  • [27] Synthesis and geometry of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-α/β-D-arabino- and -α/β-D-ribo-hexopyranosid)uronates
    Tuwalska, Dorota
    Sikorski, Artur
    Liberek, Beata
    CARBOHYDRATE RESEARCH, 2008, 343 (02) : 404 - 411
  • [28] Identification and biochemical characterization of two novel UDP-2,3-dideoxy-α-D-glucuronic acid 2-epimerases from respiratory pathogens
    Westman, Erin L.
    McNally, David J.
    Rejzek, Martin
    Miller, Wayne L.
    Kannathasan, Vellupillai Sri
    Preston, Andrew
    Maskell, Duncan J.
    Field, Robert A.
    Brisson, Jean-Robert
    Lam, Joseph S.
    BIOCHEMICAL JOURNAL, 2007, 405 (01) : 123 - 130
  • [29] Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate
    Cristofalo, Alejandro Ezequiel
    Nieto, Pedro M.
    Uhrig, Maria Laura
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 306 - 317
  • [30] First synthesis of 2-aminoacetyl-2,3-dideoxy-D-glucose
    Grove, Todd
    Witczak, Zbigniew
    Bielski, Roman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
12345