Optimized synthesis of an orthogonally protected glucosamine

被引:0
|
作者
Hernández-Torres, JM [1 ]
Liew, ST [1 ]
Achkar, J [1 ]
Wei, A [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
来源
SYNTHESIS-STUTTGART | 2002年 / 04期
关键词
carbohydrates; glucosamine; glycosides; orthogonal protecting groups;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Glucosamine hydrochloride was transformed into an orthogonally protected intermediate in seven steps and 34% overall yield. The synthesis includes an optimized preparation of N-phthaloyl-beta-D-glucosamine tetraacetate, a commonly used precursor in carbohydrate chemistry.
引用
收藏
页码:487 / 490
页数:4
相关论文
共 50 条
  • [1] Synthesis of orthogonally protected τ-histidinoalanine
    Taylor, Carol M.
    Batton, Chyree S.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] Synthesis of Orthogonally Protected Labionin
    Lo Presti, Eliana
    Volonterio, Alessandro
    Sani, Monica
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05): : 4313 - 4319
  • [3] Synthesis of orthogonally protected lanthionines
    Mustapa, MFM
    Harris, R
    Bulic-Subanovic, N
    Elliott, SL
    Bregant, S
    Groussier, MFA
    Mould, J
    Schultz, D
    Chubb, NAL
    Gaffney, PRJ
    Driscoll, PC
    Tabor, AB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21): : 8185 - 8192
  • [4] An efficient synthesis of orthogonally protected spermidine
    Amssoms, K
    Augustyns, K
    Yamani, A
    Zhang, M
    Haemers, A
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (03) : 319 - 328
  • [5] Synthesis of orthogonally protected and functionalized bacillosamines
    van Mechelen, Jeanine
    Voorneveld, Jim
    Overkleeft, Hermen S.
    Filippov, Dmitri V.
    van der Marel, Gijsbert A.
    Codee, Jeroen D. C.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2834 - 2837
  • [6] The stereospecific synthesis of 'orthogonally' protected lanthionines
    Swali, V
    Matteucci, M
    Elliot, R
    Bradley, M
    [J]. TETRAHEDRON, 2002, 58 (44) : 9101 - 9109
  • [7] Stereoselective synthesis of orthogonally protected α-methylnorlanthionine
    Avenoza, Alberto
    Busto, Jesuus H.
    Jimenez-Oses, Gonzalo
    Peregrina, Jesus M.
    [J]. ORGANIC LETTERS, 2006, 8 (13) : 2855 - 2858
  • [8] Rapid synthesis of oligomannosides with orthogonally protected monosaccharides
    Chang, Sue-Ming
    Tu, Zhijay
    Jan, Hau-Ming
    Pan, Jia-Fu
    Lin, Chun-Hung
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (39) : 4265 - 4267
  • [9] Synthesis of Orthogonally Protected Disulfide Bridge Mimetics
    Tadd, Andrew C.
    Meinander, Kristian
    Luthman, Kristina
    Wallen, Erik A. A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 673 - 675
  • [10] Versatile synthesis of orthogonally protected azamacrocyclic ligands
    Wasilewski, Matthew S.
    Wetzler, Modi M.
    Brumaghim, Julia L.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247