methyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside | 212394-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside
• 英文别名: Methyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1-thio-3,4,6-tri-O-acetyl-β-D-glucopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino]-6-methylsulfanyloxan-2-yl]methyl acetate
• CAS: 212394-19-9
• 化学式: C₂₃H₃₃NO₉S
• 分子量: 499.582
• InChiKey: GBQNVBXWPVLWMI-FYKMYLNBSA-N

物化性质

• 沸点：
  606.6±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  134.3
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到2-溴-5-羟基苯甲腈
  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：

  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 、 potassium carbonate 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.83h， 生成 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-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

文献信息

• 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。
• US6462183B1
  申请人：——

  公开号：US6462183B1

  公开（公告）日：2002-10-08