Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3•Et2O

被引:115
|
作者
Debenham, SD [1 ]
Toone, EJ [1 ]
机构
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0957-4166(99)00584-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The 4,6-di-O-benzylidene acetals of glucose, mannose, glucosamine, and galactose were regioselectively reduced by triethylsilane in the presence of BF3. Et2O to yield the 6-O-benzyl ethers in good to excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:385 / 387
页数:3
相关论文
共 50 条
  • [21] An alternative method for the highly selective iodination of alcohols using a CsI/BF3•Et2O system
    Hayat, S
    Atta-ur-Rahman
    Khan, KM
    Choudhary, MI
    Maharvi, GM
    Zia-Ullah
    Bayer, E
    SYNTHETIC COMMUNICATIONS, 2003, 33 (14) : 2531 - 2540
  • [22] BF3•Et2O promoted conjugate addition of ethanethiol to electron-deficient alkynes
    Zhou, Qing Fa
    Chu, Xue Ping
    Zhao, Shen
    Lu, Tao
    Tang, Wei Fang
    CHINESE CHEMICAL LETTERS, 2012, 23 (06) : 639 - 642
  • [23] Reactions of α-4(20)-epoxy-5-O-mesyltriacetyltaxicine I induced by BF3•Et2O/Bu4NBr
    Ferjancic, Zorana
    Matovic, Radomir
    Cekovic, Zivorad
    Saicic, Radomir N.
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (07) : 705 - 711
  • [25] Direct Assembly of Polyarenes via C-C Coupling Using PIFA/BF3•Et2O
    Faggi, Enrico
    Sebastian, Rosa M.
    Pleixats, Roser
    Vallribera, Adelina
    Shafir, Alexandr
    Rodriguez-Gimeno, Alejandra
    Ramirez de Arellano, Carmen
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) : 17980 - 17982
  • [26] The unexpected course of the reaction of steroid sapogenins with diacetoxyiodobenzene and BF3•Et2O in formic acid
    Iglesias-Arteaga, Martin A.
    Arcos-Ramos, Rafael O.
    Mendez-Stivalet, Jose M.
    TETRAHEDRON LETTERS, 2007, 48 (42) : 7485 - 7488
  • [27] Unprecedented formation of isoxazole in the reaction between nitromethane and BF3•Et2O in the presence of ethylene
    Davies, JA
    Petersohn, C
    Kukushkin, VY
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19): : 3139 - 3140
  • [28] Electrosynthesis of highly conducting poly(1,5-dihydroxynaphthalene) in BF3•Et2O
    Lu, Baoyang
    Zeng, Liqiang
    Xu, Jingkun
    Le, Zhanggao
    Rao, Huoyu
    EUROPEAN POLYMER JOURNAL, 2009, 45 (08) : 2279 - 2287
  • [29] Direct Arylation of Oligonaphthalenes Using PIFA/BF3•Et2O: From Double Arylation to Larger Oligoarene Products
    Guo, Wusheng
    Faggi, Enrico
    Sebastian, Rosa M.
    Vallribera, Adelina
    Pleixats, Roser
    Shafir, Alexandr
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16): : 8169 - 8175
  • [30] BF3•Et2O and trifluoroacetic acid/triethyl amine-mediated synthesis of functionalized piperidines
    Mohite, Amar R.
    Sultane, Prakash R.
    Bhat, Ramakrishna G.
    TETRAHEDRON LETTERS, 2012, 53 (01) : 30 - 35