A one-pot synthesis of novel N,N-dialkyl-S-glycosylsulfenamides

被引：11
|
作者：
Owen, DJ [1 ]
von Itzstein, M [1 ]
机构：
[1] Monash Univ, Dept Med Chem, Parkville, Vic 3052, Australia
来源：
CARBOHYDRATE RESEARCH | 2000年 / 328卷 / 03期
关键词：
sulfenamides; anomeric position; synthesis;
D O I：
10.1016/S0008-6215(00)00110-5
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
An efficient new entry into N,N-dialkyl-S-glycosylsulfenamides is reported. The reaction of bis-activated alkyl halides in the presence of a secondary amine base with glycosylic S-acetyl derivatives (1-S-acetyl-1-thioaldoses or 2-S-acetyl-2-thioketoses) results in the formation of novel carbohydrate sulfenamides. These new carbohydrate-based sulfenamides may provide useful derivatives with biological activity, as well as provide reactive carbohydrate sulfenylating agents. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：287 / 292
页数：6
相关论文
共 50 条
  • [41] One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
    Zupanc, Anze
    Jereb, Marjan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08): : 5991 - 6000
  • [42] One-pot synthesis of N-allylthioureas using supported reagents
    Aoyama, T
    Murata, S
    Nagata, Y
    Takido, T
    Kodomari, M
    [J]. TETRAHEDRON LETTERS, 2005, 46 (29) : 4875 - 4878
  • [43] Efficient one-pot synthesis of N-ethyl amino acids
    Rückle, T
    Dubray, B
    Hubler, F
    Mutter, M
    [J]. JOURNAL OF PEPTIDE SCIENCE, 1999, 5 (01) : 56 - 58
  • [44] A novel stereoselective one-pot conversion of alcohols into alkyl halides mediated by N,N′-diisopropylcarbodiimide
    Crosignani, S
    Nadal, B
    Li, ZN
    Linclau, B
    [J]. CHEMICAL COMMUNICATIONS, 2003, (02) : 260 - 261
  • [45] Convenient one-pot synthesis of N-aryl-3-pyrrolines.
    Venkatachalam, CS
    Jayaprakash, K
    Balasubramanian, KK
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U218 - U218
  • [46] One-Pot Synthesis and Applications of N-Heteroaryl Iodonium Salts
    Bielawski, Marcin
    Malmgren, Joel
    Pardo, Leticia M.
    Wikmark, Ylva
    Olofsson, Berit
    [J]. CHEMISTRYOPEN, 2014, 3 (01): : 19 - 22
  • [47] One-pot synthesis of N-substituted phthalimides from methylarenes
    de Silva, S
    Dhruve, S
    Isidor, D
    Nyakirang'ani, M
    Pathirana, S
    Klu, E
    Osinaiya, T
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U129 - U129
  • [48] Rearrangement of propargylamine N-oxides and a one-pot synthesis of Celecoxib
    Chen, Jinshan
    Properzi, Roberta
    Dushin, Russell G.
    Uccello, Daniel P.
    Starr, Jeremy T.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [49] One-pot and microwave-assisted synthesis of N-sulfonylaziridines
    Xu, Hao
    Tian, Hua
    Zheng, Liangyu
    Liu, Qingwen
    Wang, Li
    Zhang, Suoqin
    [J]. TETRAHEDRON LETTERS, 2011, 52 (22) : 2873 - 2875
  • [50] One-pot synthesis of N-substituted pantolactams from pantolactone
    Barrios, I
    Camps, P
    Comes-Franchini, M
    Muñoz-Torrero, D
    Ricci, A
    Sánchez, L
    [J]. TETRAHEDRON, 2003, 59 (11) : 1971 - 1979
12345