3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide | 212394-16-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-α-D-glucopyranosyl bromide；2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino]oxan-2-yl]methyl acetate
• CAS: 212394-16-6
• 化学式: C₂₂H₃₀BrNO₉
• 分子量: 532.385
• InChiKey: WIWRBCNYMMWKAR-MLZLACJZSA-N

物化性质

• 沸点：
  589.8±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide 在 sodium metabisulfite 、 氨 、 sodium methylate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 丙酮 、 乙腈 为溶剂， 反应 20.83h， 生成 methyl 2-amino-2-deoxy-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Dde as a Protecting Group for Carbohydrate Synthesis

  摘要：

  Oligosaccharide synthesis using aminosugars requires the presence of a suitable amino protecting group. A number of protecting groups are currently used, and while many display favorable properties, most agents available still suffer from certain disadvantages. This report details the use of a hydrazine labile aminosugar protecting group, N -[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl] (Dde), which can be introduced and removed in a facile and cost-effective manner.

  DOI：

  10.1080/07328300500388685
• 作为产物：
  描述：

  2-乙酰基-5,5-二甲基-1,3-环己二酮 在 吡啶 、 氢溴酸 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Dde as a Protecting Group for Carbohydrate Synthesis

  摘要：

  Oligosaccharide synthesis using aminosugars requires the presence of a suitable amino protecting group. A number of protecting groups are currently used, and while many display favorable properties, most agents available still suffer from certain disadvantages. This report details the use of a hydrazine labile aminosugar protecting group, N -[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl] (Dde), which can be introduced and removed in a facile and cost-effective manner.

  DOI：

  10.1080/07328300500388685

文献信息

• Combinatorial libraries of monosaccharides
  申请人：——

  公开号：US20030232766A1

  公开（公告）日：2003-12-18

  A monosaccharide compound of formula I as shown in the specification. Processes for the preparation of the compound of formula I and methods of screening for antibacterial or antibiotic compounds involving the compound of formula I.

  在规范中显示的式I的单糖化合物。制备式I化合物的方法以及涉及式I化合物的抗菌或抗生素化合物筛选方法。
• Protected aminosugars
  申请人：Alchemia Pty Ltd

  公开号：US06462183B1

  公开（公告）日：2002-10-08

  The invention provides amine-protecting groups for use in solution phase or solid-phase oligosaccharide synthesis, in which a 2-substituted 1,3-dioxo compound is used to protect one or more primary amine groups of an aminosugar or gylycosylamine. The invention provides reagents, reagent kits, and methods for solution phase, solid-phase oligosaccharide synthesis.

  该发明提供了用于溶液相或固相寡糖合成中的胺保护基，其中使用2-取代的1,3-二氧化合物来保护氨基糖或甘氨基胺的一个或多个主要胺基团。该发明提供了用于溶液相、固相寡糖合成的试剂、试剂盒和方法。
• MONOSACCHARIDE COMPOUNDS AND METHODS THEREFOR
  申请人：West Michael Leo

  公开号：US20100184607A1

  公开（公告）日：2010-07-22

  A monosaccharide compound of formula I as shown in the specification. Processes for the preparation of the compound of formula I and methods of screening for antibacterial or antibiotic compounds involving the compound of formula I.

  一种单糖化合物，其化学式I如规范中所示。制备化学式I化合物的方法以及涉及化学式I化合物的抗菌或抗生素化合物筛选方法。
• Monosaccharide compounds and methods therefor
  申请人：Alchemia Pty Ltd

  公开号：US08093227B2

  公开（公告）日：2012-01-10

  A monosaccharide compound of formula I as shown in the specification. Processes for the preparation of the compound of formula I and methods of screening for antibacterial or antibiotic compounds involving the compound of formula I.

  一种单糖化合物，其化学式I如规范中所示。制备化学式I化合物的工艺以及涉及化学式I化合物的抗菌或抗生素化合物筛选方法。
• US6462183B1
  申请人：——

  公开号：US6462183B1

  公开（公告）日：2002-10-08