Efficient acid-promoted per-O-sulfation of organic polyols

被引：37
作者：
Krylov, Vadim B. [1 ]
Ustyuzhanina, Nadezhda E. [1 ]
Grachev, Alexey A. [1 ]
Nifantiev, Nikolay E. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 41期
关键词：
sulfation; carbohydrates; lignans; flavonoids; cyclitols;
D O I：
10.1016/j.tetlet.2008.07.135
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the preparation of per-O-sulfated organic compounds is reported. Sulfation of polyols with the Et3N center dot SO3 complex in DMF in the presence of triflic acid allowed acceleration of the reaction at lower temperature. The efficiency of the developed protocol is demonstrated by the transformation of a series of organic polyols and phenols related to oligosaccharides, cyclitols, lignans and flavonoids. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5877 / 5879
页数：3
相关论文
共 17 条
  • [1] Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide
    Berteau, O
    Mulloy, B
    [J]. GLYCOBIOLOGY, 2003, 13 (06) : 29R - 40R
  • [2] CORREIADASILVA M, 2008, 1 INT C DRUG DES DIS, P31
  • [3] A comparative study of the anti-inflammatory, anticoagulant, antiangiogenic, and antiadhesive activities of nine different fucoidans from brown seaweeds
    Cumashi, Albana
    Ushakova, Natalia A.
    Preobrazhenskaya, Marina E.
    D'Incecco, Armida
    Piccoli, Antonio
    Totani, Licia
    Tinari, Nicola
    Morozevich, Galina E.
    Berman, Albert E.
    Bilan, Maria I.
    Usov, Anatolii I.
    Ustyuzhanina, Nadezhda E.
    Grachev, Alexey A.
    Sanderson, Craig J.
    Kelly, Maeve
    Rabinovich, Gabriel A.
    Iacobelli, Stefano
    Nifantiev, Nikolay E.
    [J]. GLYCOBIOLOGY, 2007, 17 (05) : 541 - 552
  • [4] Assessment through chemical synthesis of the size of the heparin sequence involved in thrombin inhibition
    Duchaussoy, P
    Jaurand, G
    Driguez, PA
    Lederman, I
    Ceccato, ML
    Gourvenec, F
    Strassel, JM
    Sizun, P
    Petitou, M
    Herbert, JM
    [J]. CARBOHYDRATE RESEARCH, 1999, 317 (1-4) : 85 - 99
  • [5] Synthesis and heparanase inhibitory activity of sulfated mannooligosaccharides related to the antiangiogenic agent PI-88
    Fairweather, Jon K.
    Hammond, Edward
    Johnstone, Ken D.
    Ferro, Vito
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) : 699 - 709
  • [6] FATIADI AJ, 1970, J CARBOHYDR RES, V12, P293
  • [7] Synthesis, NMR, and conformational studies of fucoidan fragments.: V.: Linear 4,4′,4"-Tri-O-sulfated and parent non-sulfated (1→3)-fucotrioside fragments
    Gerbst, AG
    Ustuzhanina, NE
    Grachev, AA
    Khatuntseva, EA
    Tsvetkov, DE
    Shashkov, AS
    Usov, AI
    Preobrazhenskaya, ME
    Ushakova, NA
    Nifantiev, NE
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 2003, 22 (02) : 109 - 122
  • [8] Synthesis, NMR, and conformational studies of fucoidan fragments.: IV.: 4-mono- and 4,4'-disulfated (1→3)-α-L-fucobioside and 4-sulfated fucoside fragments
    Gerbst, AG
    Ustuzhanina, NE
    Grachev, AA
    Zlotina, NS
    Khatuntseva, EA
    Tsvetkov, DE
    Shashkov, AS
    Usov, AI
    Nifantiev, NE
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 2002, 21 (04) : 313 - 324
  • [9] Synthesis and biological activities of octyl 2,3,4-tri-O-sulfo-α-L-fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-α-L-fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-α-L-fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-β-L-fucopyranoside
    Hua, YX
    Gu, GF
    Du, YG
    [J]. CARBOHYDRATE RESEARCH, 2004, 339 (04) : 867 - 872
  • [10] Synthesis of 2,5-anhydro-(β-D-glueopyranosyluronate)- and (α-L-idopyranosyluronate)-D-mannitol hexa-O-sulfonate hepta sodium salt
    Kuszmann, J
    Medgyes, G
    Boros, S
    [J]. CARBOHYDRATE RESEARCH, 2004, 339 (08) : 1569 - 1579
12