Synthesis of New [(2S)-N-(p-Tolylsulfonyl)-2-Pyrrolidinyl]Propyl 2,3,4-Tri-O-Acetyl- and 2,3,4-Tri-O-Benzyl-β-L-Fucopyranosides

被引:0
作者
Joselice e Silva, Maria [1 ]
Srivastava, Rajendra M. [1 ]
Doboszewski, Bogdan [2 ]
Cottier, Louis [3 ]
Sinou, Denis [3 ]
机构
[1] Univ Fed Pernambuco, Dept Quim Fundamental, BR-50740540 Recife, PE, Brazil
[2] Univ Fed Pernambuco, Dept Quim, BR-50740540 Recife, PE, Brazil
[3] Univ Lyon 1, Lab Synth Asymetr, CNRS UMR 5181, ESCPE Lyon, F-69622 Villeurbanne, France
关键词
L-Proline; delta-amino alcohol; O-alpha-L-fucosyltrichloroacetimidate; beta-L-fucopyranoside; glycosylation; OLIGOSACCHARIDE SYNTHESIS; GLYCOSYLATION; TRICHLOROACETIMIDATE; PYRROLIDINE; CLEAVAGE;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of two new glycoheterocyclic compounds, [(2S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl 2,3,4-tri-O-acetyl- and 2,3,4-tri-O-benzyl-beta-L-fucopyranosides 1a and 1b, starting from 6-amino alcohol (-)-[(2S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propan-1-ol 2 and O-alpha-L-fucosyltrichloroacetimidates 3a or 3b as glycosyl donor is described. Hitherto delta-aminoalcohol 2 was synthesized from L-proline without any racemization during its preparation.
引用
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页码:105 / 111
页数:7
相关论文
共 20 条
  • [1] STANNIC TETRACHLORIDE CATALYZED GLYCOSYLATION OF 8-ETHOXYCARBONYLOCTANOL BY CELLOBIOSE, LACTOSE, AND MALTOSE OCTAACETATES - SYNTHESIS OF ALPHA-GLYCOSIDIC AND BETA-GLYCOSIDIC LINKAGES
    BANOUB, J
    BUNDLE, DR
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16): : 2085 - 2090
  • [2] Carmona AT, 2008, CURR ORG SYNTH, V5, P33
  • [3] Thioglycosides in sequential glycosylation strategies
    Codée, JDC
    Litjens, REJN
    van den Bos, LJ
    Overkleeft, HS
    van der Marel, GA
    [J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (09) : 769 - 782
  • [4] Recent developments in oligosaccharide synthesis
    Davis, BG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14): : 2137 - 2160
  • [5] ASYMMETRIC-SYNTHESIS - METAL-COMPLEX MEDIATED SYNTHESIS OF CHIRAL GLYCINE BY ENANTIOSELECTIVE PROTON-EXCHANGE
    DOKUZOVIC, Z
    ROBERTS, NK
    SAWYER, JF
    WHELAN, J
    BOSNICH, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2034 - 2039
  • [6] SELECTIVE CLEAVAGE OF ANOMERIC ACETYL GROUPS OF ACETYLATED GLYCOSYL RESIDUES BY HYDRAZINE
    EXCOFFIER, G
    GAGNAIRE, D
    UTILLE, JP
    [J]. CARBOHYDRATE RESEARCH, 1975, 39 (02) : 368 - 373
  • [7] Fraser-Reid B., 1999, BIOORGANIC CHEM CARB, P89
  • [8] CLEAVAGE OF SULFONAMIDES WITH SODIUM NAPHTHALENE
    JI, S
    GORTLER, LB
    WARING, A
    BATTISTI, A
    BANK, S
    CLOSSON, WD
    WRIEDE, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) : 5311 - &
  • [9] Synthesis, NMR and conformational studies of fucoidan fragments 1: Desulfated 2,3-and 3,4-branched trisaccharide fragments and constituting disaccharides
    Khatuntseva, EA
    Ustuzhanina, NE
    Zatonskii, GV
    Shashkov, AS
    Usov, AI
    Nifant'ev, NE
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 2000, 19 (09) : 1151 - 1173
  • [10] MUNOZ O, 1994, LIEBIGS ANN CHEM, P521