A convenient method for the alkylation of sulfamides using alkyl bromides and Mitsunobu betaine

被引：10
作者：
Winum, JY [1 ]
Barragan, V [1 ]
Montero, JL [1 ]
机构：
[1] Univ Montpellier 2, UMR 5032, Lab Chim Biomol, F-34095 Montpellier 05, France
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 04期
关键词：
sulfamides; Mitsunobu betaine; glycosylation; alkyl bromide;
D O I：
10.1016/S0040-4039(00)02012-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alkylation of N-Boc-N'-(2-chloroethyl)sulfamide 1 by electron-deficient alkyl bromides using the Mitsunobu reagent as mild base is described. This method was also applied to the N-glycosylation of various carbohydrates and was anomerically selective. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：601 / 603
页数：3
相关论文
共 16 条
  • [1] Synthesis of 2-chloroethylnitrososulfamides (CENS) via a transsulfamoylation reaction
    Abdaoui, M
    Dewynter, G
    Aouf, N
    Montero, JL
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 118 : 39 - 47
  • [2] Synthesis and structure of 2-chloroethylnitrososulfamides (CENS) derived from amino acids. Part 5
    Abdaoui, M
    Dewynter, G
    Toupet, L
    Montero, JL
    [J]. TETRAHEDRON, 2000, 56 (16) : 2427 - 2435
  • [3] New family of potential oncostatics: 2-Chloroethylnitrososulfamides (CENS) .1. Synthesis, structure, and pharmacological evaluation - (Preliminary results)
    Abdaoui, M
    Dewynter, G
    Aouf, N
    Favre, G
    Morere, A
    Montero, JL
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (08) : 1227 - 1235
  • [4] Expedient synthesis of 2-chloroethylnitrososulfamides (CENS) via the decarboxylative reopening of sulfamoyloxazolidinones
    Abdaoui, M
    Dewynter, G
    Montero, JL
    [J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5695 - 5698
  • [5] SYNTHESIS OF PYRAZOMYCINS
    DEBERNARDO, S
    WEIGELE, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) : 287 - 290
  • [6] Synthesis of N-sulfamoyloxazolidinones and -perhydrooxazinones reactivity and use as donors in the Transsulfamoylation reaction; Application to the preparation of 2-chloroethylnitrososulfamides .4.
    Dewynter, G
    Abdaoui, M
    Regainia, Z
    Montero, JL
    [J]. TETRAHEDRON, 1996, 52 (45) : 14217 - 14224
  • [7] NOVEL SYNTHESIS OF ARYL GLYCOSIDES
    GRYNKIEWICZ, G
    [J]. CARBOHYDRATE RESEARCH, 1977, 53 (01) : C11 - C12
  • [8] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
    HENRY, JR
    MARCIN, LR
    MCINTOSH, MC
    SCOLA, PM
    HARRIS, GD
    WEINREB, SM
    [J]. TETRAHEDRON LETTERS, 1989, 30 (42) : 5709 - 5712
  • [9] Hughes D.L., 1992, ORG REACT, V42, P335, DOI DOI 10.1002/0471264180.OR042.02
  • [10] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS
    MITSUNOBU, O
    [J]. SYNTHESIS-STUTTGART, 1981, (01): : 1 - 28
12