Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals

被引：27
作者：
Sarpe, Vikram A. [1 ]
Kulkarni, Suvarn S. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 38期
关键词：
DIACYLTREHALOSE GLYCOLIPIDS; OLIGOSACCHARIDES; ANALOGS; CLEAVAGE; MARADOLIPIDS; DERIVATIVES;
D O I：
10.1039/c3ob41389f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including a mycobacterial trisaccharide, a 4-epi-trehalosamine analog and a maradolipid.
引用
收藏
页码：6460 / 6465
页数：6
相关论文
共 51 条
  • [1] Uptake of unnatural trehalose analogs as a reporter for Mycobacterium tuberculosis
    Backus, Keriann M.
    Boshoff, Helena L.
    Barry, Conor S.
    Boutureira, Omar
    Patel, Mitul K.
    D'Hooge, Francois
    Lee, Seung Seo
    Via, Laura E.
    Tahlan, Kapil
    Barry, Clifton E., III
    Davis, Benjamin G.
    [J]. NATURE CHEMICAL BIOLOGY, 2011, 7 (04) : 228 - 235
  • [2] SYNTHESIS OF MIRROR CORYNO CORD FACTORS
    BAER, HH
    SHEN, YP
    WU, XF
    [J]. CARBOHYDRATE RESEARCH, 1993, 241 : 117 - 129
  • [3] AN IMPROVED SYNTHESIS OF 4-AZIDO-4-DEOXY-ALPHA,ALPHA-TREHALOSE AND 4-AMINO-4-DEOXY-ALPHA,ALPHA-TREHALOSE AND THEIR EPIMERS
    BASSILY, RW
    ELSOKKARY, RI
    SILWANIS, BA
    NEMATALLA, AS
    NASHED, MA
    [J]. CARBOHYDRATE RESEARCH, 1993, 239 : 197 - 207
  • [4] CHARACTERIZATION OF THE SPECIFIC ANTIGENICITY OF MYCOBACTERIUM-FORTUITUM
    BESRA, GS
    MCNEIL, MR
    BRENNAN, PJ
    [J]. BIOCHEMISTRY, 1992, 31 (28) : 6504 - 6509
  • [5] Iron(III) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides
    Bourdreux, Yann
    Lemetais, Aurelie
    Urban, Dominique
    Beau, Jean-Marie
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (07) : 2146 - 2148
  • [6] BRENNAN PJ, 1989, REV INFECT DIS, V11, pS420
  • [7] Chaube M. A., 2012, TRENDS CARBOHYDR RES, V4, P1
  • [8] Synthesis of a maradolipid without using protecting groups
    Csuk, Rene
    Schultheiss, Andrea
    Sommerwerk, Sven
    Kluge, Ralph
    [J]. TETRAHEDRON LETTERS, 2013, 54 (18) : 2274 - 2276
  • [9] A METHOD FOR THE SELECTIVE REDUCTION OF CARBOHYDRATE 4,6-O-BENZYLIDENE ACETALS
    DENINNO, MP
    ETIENNE, JB
    DUPLANTIER, KC
    [J]. TETRAHEDRON LETTERS, 1995, 36 (05) : 669 - 672
  • [10] Molecular design and biological potential of galacto-type trehalose as a nonnatural ligand of Shiga toxins
    Dohi, H
    Nishida, Y
    Furuta, Y
    Uzawa, H
    Yokoyama, S
    Ito, S
    Mori, H
    Kobayashi, K
    [J]. ORGANIC LETTERS, 2002, 4 (03) : 355 - 357
123456