2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate | 212394-26-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-3,4,6-tri-O-acetyl-α,β-D-glucopyranosyl trichloroacetimidate；[(2R,3S,4R,5R)-3,4-diacetyloxy-5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino]-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 212394-26-8
• 化学式: C₂₄H₃₁Cl₃N₂O₁₀
• 分子量: 613.877
• InChiKey: OQUKAWCEUMRCQH-LIDDZCSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  167.38
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate 、 联苯-4-甲醇 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 4-phenylbenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-β-D-glucopyranoside 、 4-phenylbenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-α-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 哌啶 、 吡啶 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate
  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.

  本发明提供了一种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1,3-二氧杂环化合物来保护氨基糖或糖氨基的一个或多个主要胺基团。本发明提供了溶液相、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