2-C-branched glycosides from 2'-carbonylalkyl 2-O-Ms(Ts)-C-glycosides.: A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars

被引：32
|
作者：
Shao, HW
Ekthawatchai, S
Wu, SH
Zou, W
机构：
[1] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada
[2] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 20期
关键词：
D O I：
10.1021/ol0486627
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Under basic conditions, 2'-aldehydo (acetonyl) 2-O-Ms(Ts)-alpha-C-glycosides undergo an intramolecular S(N)2 reaction to form 1,2-cyclopropanated sugars, which react with nucleophiles (alcohols, thiols, and azide) at the anomeric carbon to give 2-C-branched glycosides. By way of contrast, the 1,2-cyclopropanes derived from 2'-ketones only react with thiols to give 2-C-branched thioglycosides.
引用
收藏
页码：3497 / 3499
页数：3
相关论文
共 50 条
  • [31] Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-C-Branched Glycosides (vol 13, pg 5088, 2011)
    Yin, Biao-Lin
    Zhang, Ze-Ren
    Xu, Li-Wen
    Jiang, Huanfeng
    ORGANIC LETTERS, 2012, 14 (04) : 1186 - 1186
  • [32] Tetracarbonyl-1κ2C,3κ2C-bis[1,3(η5)-cyclopentadienyl]dihydroxido-2κ2O-diirontin(2 Fe-Sn) monohydrate
    Koessel, Stefanie
    Wagner, Christoph
    Merzweiler, Kurt
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : M811 - U875
  • [33] SYNTHESIS OF BETA-D-MANNOSIDES FROM BETA-D-GLUCOSIDES VIA AN INTRAMOLECULAR SN2 REACTION AT C-2
    GUNTHER, W
    KUNZ, H
    CARBOHYDRATE RESEARCH, 1992, 228 (01) : 217 - 241
  • [34] VINYLIC CATIONS FROM SOLVOLYSIS .2. STEREOCHEMISTRY OF SN1 REACTION OF 1,2-DIANISYL-2-PHENYLVINYL HALIDES
    RAPPOPOR.Z
    APELOIG, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (24) : 6734 - +
  • [35] "CO" as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki-Miyaura Reaction from 2-Iodoglycals
    de Robichon, Morgane
    Bordessa, Andrea
    Lubin-Germain, Nadege
    Ferry, Angelique
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06): : 3328 - 3339
  • [36] Modular Stereoselective Synthesis of (1→2)-C-Glycosides based on the sp2-sp3 Suzuki-Miyaura Reaction
    Oroszova, Beata
    Choutka, Jan
    Pohl, Radek
    Parkan, Kamil
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (19) : 7043 - 7047
  • [37] Polishing of PbTe and Pb1-x Sn x Te surfaces with H2O2-HBr-C2H2O4 solutions
    Malanych, G. P.
    Tomashyk, V. N.
    Stratiychuk, I. B.
    Tomashyk, Z. F.
    INORGANIC MATERIALS, 2015, 51 (01) : 15 - 19
  • [38] Synthesis of 2-deoxy-C-glycosides via Lewis acid-mediated rearrangement of 2,3-anhydro-1-thiopyranosides
    Xiong, De-Cai
    Gao, Chao
    Li, Wenming
    Wang, Yuan
    Li, Qin
    Ye, Xin-Shan
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (07): : 798 - 806
  • [39] A new approach to Amadori ketoses via MoVI-catalyzed stereospecific isomerization of 2-C-branched sugars bearing azido function in a microwave field
    Hricoviniova, Zuzana
    TETRAHEDRON-ASYMMETRY, 2010, 21 (18) : 2238 - 2243
  • [40] SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF [SN(1,2-O2C6H3NO2-4)(C4H8O)]N - A TIN(II) CATECHOL COMPLEX
    MACHELL, JC
    MINGOS, DMP
    STOLBERG, TL
    POLYHEDRON, 1989, 8 (24) : 2933 - 2935
12345