The 2-(allyloxy) phenyl acetyl ester as a new relay protecting group for oligosaccharide synthesis

被引:16
|
作者
Arranz, E [1 ]
Boons, GJ [1 ]
机构
[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA
关键词
D O I
10.1016/S0040-4039(01)01303-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2-(allyloxy) phenyl acetyl group can be removed by a relay approach using Pd(PPh3)(4) in combination with proton sponge, conditions that do not affect acetyl, benzoyl and levulinoyl esters. On the other hand, the acetyl and levulinoyl ester could be cleaved without removal of the 2-(allyloxy) phenyl acetyl group. The new protecting group is compatible with glycosylations and can perform efficiently neighboring group participation leading to the exclusive formation of 1,2-trans glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6469 / 6471
页数:3
相关论文
共 50 条
  • [31] SYNTHESIS OF OLIGODEOXYNUCLEOTIDES WITH 2-(ALPHA-PYRIDYL)ETHANOL AS PHOSPHATE PROTECTING GROUP
    FREIST, W
    CRAMER, F
    CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (10): : 3122 - &
  • [32] THE 2-(METHYLTHIOMETHOXY) ETHOXYCARBONYL [MTMEC] PROTECTING GROUP
    JONES, SS
    REESE, CB
    SIBANDA, S
    TETRAHEDRON LETTERS, 1981, 22 (20) : 1933 - 1936
  • [33] A new water-soluble N-protecting group, 2-(phenyl(methyl)sulfonio)ethyloxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water
    Hojo, K
    Maeda, M
    Kawasaki, K
    JOURNAL OF PEPTIDE SCIENCE, 2001, 7 (12) : 615 - 618
  • [34] 2-(Prenyloxymethyl)benzoyl (POMB) group:: a new temporary protecting group removable by intramolecular cyclization
    Vatele, Jean-Michel
    TETRAHEDRON, 2007, 63 (45) : 10921 - 10929
  • [35] THE 2-(DIPHENYLPHOSPHINO) ETHYL GROUP (DPPE) AS A NEW CARBOXYL-PROTECTING GROUP IN PEPTIDE CHEMISTRY
    CHANTREUX, D
    GAMET, JP
    JACQUIER, R
    VERDUCCI, J
    TETRAHEDRON, 1984, 40 (16) : 3087 - 3094
  • [36] PROTECTING GROUP DEPENDENT REVERSAL OF ENANTIOSELECTIVITY IN THE ASYMMETRIC ESTER ENOLATE-IMINE CYCLOCONDENSATION - SYNTHESIS OF 3-HYDROXY-4-PHENYL-2-AZETIDINONES
    BOGE, TC
    GEORG, GI
    CHERUVALLATH, ZS
    HARRIMAN, GCB
    HEPPERLE, M
    PARK, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 237 - MEDI
  • [37] 4-Acetyl-3-[2-(ethoxycarbonyl)phenyl]sydnone
    Grossie, David
    Harrison, Leanna
    Turnbull, Kenneth
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1662 - +
  • [38] Synthesis of 2-(2,4-dinitrophenylsulphonyl) ethyloxycarbonyl chloride: A reagent for introducing a new base labile amino protecting group for peptide synthesis
    Gurnani, J
    Narang, CK
    Sherwani, MRK
    HUNGARIAN JOURNAL OF INDUSTRIAL CHEMISTRY, 1999, 27 (01): : 1 - 3
  • [39] 2-(4-tolylsulfonyl)ethoxymethyl (TEM) -: a new 2′-OH protecting group for solid-supported RNA synthesis
    Zhou, Chuanzheng
    Honcharenko, Dmytro
    Chattopadhyaya, Jyoti
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (02) : 333 - 343
  • [40] Synthesis, Structure, and Reactivity of Pentacoordinate Hydrosilanes Bearing a 2-(Phenylazo)phenyl Group
    Yamamura, Masaki
    Kano, Naokazu
    Kawashima, Takayuki
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2009, 635 (9-10): : 1295 - 1299