Direct synthesis of methyl phosphoramidates in carbohydrates

被引:8
作者
Dhurandhare, Vijay M. [1 ,2 ,3 ]
Mishra, Girija Prasad [1 ,4 ]
Lam, Sarah [1 ]
Wang, Cheng-Chung [1 ,2 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Taiwan Int Grad Program, Chem Biol & Mol Biophys, Taipei, Taiwan
[3] Natl Tsing Hua Univ, Inst Bioinformat & Struct Biol, Hsinchu 300, Taiwan
[4] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan
关键词
CAMPYLOBACTER-JEJUNI; ANALOGS; CAPSULE;
D O I
10.1039/c5ob01017a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct installation of a methyl phosphoramidate group by using methyl benzylphosphoramidochloridate into carbohydrates and amino acid is described. This one-step synthesis is efficient for both primary and secondary alcohols and exhibited excellent regioselectivity and functional group compatibility. Formation of a single diastereomer is observed in certain cases. The N-benzyl protecting group on methyl phosphoramidates is easily removed under mild conditions.
引用
收藏
页码:9457 / 9461
页数:5
相关论文
共 19 条
  • [1] Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions
    Adinolfi, M
    Barone, G
    Guariniello, L
    Iadonisi, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (48) : 8439 - 8441
  • [2] Synthesis of Carbohydrate Methyl Phosphoramidates
    Ashmus, Roger A.
    Lowary, Todd L.
    [J]. ORGANIC LETTERS, 2014, 16 (09) : 2518 - 2521
  • [3] Insect Infection Model for Campylobacter jejuni Reveals That O-methyl Phosphoramidate Has Insecticidal Activity
    Champion, Olivia L.
    Karlyshev, Andrey V.
    Senior, Nicola J.
    Woodward, Martin
    La Ragione, Roberto
    Howard, Sarah L.
    Wren, Brendan W.
    Titball, Richard W.
    [J]. JOURNAL OF INFECTIOUS DISEASES, 2010, 201 (05) : 776 - 782
  • [4] Discovery of the First C-Nucleoside HCV Polymerase Inhibitor (GS-6620) with Demonstrated Antiviral Response in HCV Infected Patients
    Cho, Aesop
    Zhang, Lijun
    Xu, Jie
    Lee, Rick
    Butler, Thomas
    Metobo, Sammy
    Aktoudianakis, Vangelis
    Lew, Willard
    Ye, Hong
    Clarke, Michael
    Doerffler, Edward
    Byun, Daniel
    Wang, Ting
    Babusis, Darius
    Carey, Anne C.
    German, Polina
    Sauer, Dorothea
    Zhong, Weidong
    Rossi, Stephen
    Fenaux, Martijn
    McHutchison, John G.
    Perry, Jason
    Feng, Joy
    Ray, Adrian S.
    Kim, Choung U.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (05) : 1812 - 1825
  • [5] Dhurandhare V. M., UNPUB
  • [6] Efficient, one-pot syntheses of biologically active α-linked glycolipids
    Du, Wenjun
    Kulkarni, Suvarn S.
    Gervay-Hague, Jacquelyn
    [J]. CHEMICAL COMMUNICATIONS, 2007, (23) : 2336 - 2338
  • [7] Campylobacter sugars sticking out
    Guerry, Patricia
    Szymanski, Christine M.
    [J]. TRENDS IN MICROBIOLOGY, 2008, 16 (09) : 428 - 435
  • [8] NATURE OF MOLECULAR-CONFORMATIONS INFERRED FROM HIGH-RESOLUTION NMR
    JARDETZKY, O
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1980, 621 (02) : 227 - 232
  • [9] Simple one-pot regioselective 6-O-phosphorylation of carbohydrates and trehalose desymmetrization
    Joseph, A. Abragam
    Chang, Chun-Wei
    Wang, Cheng-Chung
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (98) : 11497 - 11499
  • [10] The Polysaccharide Capsule of Campylobacter jejuni Modulates the Host Immune Response
    Maue, Alexander C.
    Mohawk, Krystle L.
    Giles, David K.
    Poly, Frederic
    Ewing, Cheryl P.
    Jiao, Yuening
    Lee, Ginyoung
    Ma, Zuchao
    Monteiro, Mario A.
    Hill, Christina L.
    Ferderber, Jason S.
    Porter, Chad K.
    Trent, M. Stephen
    Guerry, Patricia
    [J]. INFECTION AND IMMUNITY, 2013, 81 (03) : 665 - 672