2-溴-5-羟基苯甲腈 | 282526-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-5-羟基苯甲腈
• 英文名称: methyl 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-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino)-2-deoxy-1-thio-β-D-glucopyranoside；methyl 2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1-thio-β-D-glucopyranoside；2-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methylsulfanyloxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 282526-14-1
• 化学式: C₁₇H₂₇NO₆S
• 分子量: 373.47
• InChiKey: PXBHJZJPPCZTOI-BTAUDXDXSA-N

物化性质

• 沸点：
  594.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  116.09
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-溴-5-羟基苯甲腈 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 55.0h， 生成 methyl 3-O-benzoyl-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethylamino)-2-deoxy-4,6-bis-O-(methanesulfonyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  氨基葡萄糖转化为半乳糖胺和同素胺衍生物：控制C-3和C-4立体化学的转化。

  摘要：

  为了使人们容易地获得半乳糖胺类似物，已经研究了苯甲酸钠与一系列衍生自葡糖胺的偏苯三酸酯的反应。其中氨基被保护为邻苯二甲酰亚胺的三甲磺酸酯17，在4和6位进行了两次置换，得到具有所需半乳糖胺构型的二苯甲酸酯18。相反，其中氨基被保护为乙酰胺的均苯三甲酸酯21和27出乎意料地在位置3和6进行了两次置换，分别得到具有异源胺构型的产物22和28。

  DOI：

  10.1021/jo010210+
• 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 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.83h， 生成 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

文献信息

• Protecting groups for carbohydrate synthesis
  申请人：Dekany Gyula

  公开号：US06953850B1

  公开（公告）日：2005-10-11

  The invention provides collections of orthogonally-protected monosaccharides as universal building blocks for the synthesis of glycoconjugates of non-carbohydrate molecules, neo-glycoconjugates and oligosaccharides. This orthogonal protection strategy allows for the specific deprotection of any substituent ono the saccharide ring, and greatly facilitates targeted or library-focused carbohydrate-related syntheses. In particular, the invention provides a universal monosaccharide building block of General Formula (I) or General Formula (II) in which A is a leaving group; X is hydrogen, O, N or N 3 ; X 1 is hydrogen, —CH 2 O—, —CH 2 NH—, —CH 3 , —CH 2 N 3 or —COO—; and B, C, D and E are protecting groups that can be cleaved orthogonally, and in which B, C, D and E are absent when X is hydrogen or N 3 , and E is absent when X 1 is hydrogen, CH 3 or N 3 .

  该发明提供了一种正交保护的单糖集合，作为合成非碳水化合物分子的糖蛋白共轭物、新糖蛋白共轭物和寡糖的通用构建块。这种正交保护策略允许特异性去保护糖环上的任何取代基，并极大地促进了针对性或以库为焦点的与碳水化合物相关的合成。具体而言，该发明提供了一种通用单糖构建块，其通用公式为(I)或通用公式(II)，其中A是一个离去基团；X是氢、O、N或N3；X1是氢、-CH2O-、-CH2NH-、-CH3、-CH2N3或-COO-；B、C、D和E是可以正交裂解的保护基团，其中当X为氢或N3时，B、C、D和E不存在，当X1为氢、CH3或N3时，E不存在。
• US6953850B1
  申请人：——

  公开号：US6953850B1

  公开（公告）日：2005-10-11
• Conversion of Glucosamine to Galactosamine and Allosamine Derivatives:  Control of Inversions of Stereochemistry at C-3 and C-4
  作者：Ross P. McGeary、Karen Wright、Istvan Toth

  DOI：10.1021/jo010210+

  日期：2001.7.1

  of sodium benzoate with a series of trimesylates derived from glucosamine have been examined in an attempt to gain facile access to galactosamine analogues. Trimesylate 17, in which the amino group was protected as a phthalimide, underwent double displacement at positions 4 and 6 to give the dibenzoate 18 with the desired galactosamine configuration. In contrast, trimesylates 21 and 27, in which the

  为了使人们容易地获得半乳糖胺类似物，已经研究了苯甲酸钠与一系列衍生自葡糖胺的偏苯三酸酯的反应。其中氨基被保护为邻苯二甲酰亚胺的三甲磺酸酯17，在4和6位进行了两次置换，得到具有所需半乳糖胺构型的二苯甲酸酯18。相反，其中氨基被保护为乙酰胺的均苯三甲酸酯21和27出乎意料地在位置3和6进行了两次置换，分别得到具有异源胺构型的产物22和28。
• Dde as a Protecting Group for Carbohydrate Synthesis
  作者：Laurent Bornaghi、Guyla Dekany、Nicholas B. Drinnan、Stephen Taylor、Istvan Toth、Michael L. West

  DOI：10.1080/07328300500388685

  日期：2006.1.1

  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.