2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-galactopyranose-1,3,4,6-tetraacetate | 5348-99-2

• 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: 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-galactopyranose-1,3,4,6-tetraacetate
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-(((benzyloxy)carbonyl)amino)-2-deoxy-α-D-glucopyranose (en).α.-D-Glucopyranose, 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 1,3,4,6-tetraacetate (en)；1,3,4,6-tetra-O-acetyl-2-(((benzyloxy)carbonyl)amino)-2-deoxy-β-D-glucopyranose (en).β.-D-Glucopyranose, 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-, 1,3,4,6-tetraacetate (en)；1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside；1,3,4,6-tetra-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose；1,3,4,6-tetra-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-D-glucopyranose；1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-D-glucopyranoside；1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-D-glucopyranose；2-benzyloxycarbonylamino-2-deoxy-1,3,4,6-tetra-O-acetyl-glucopyranose；α/β-1,3,4,6-Tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-D-glucose
• CAS: 5348-99-2；35946-66-8；82264-19-5；100483-05-4
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: WFUOWCBLXHATHL-CVNCVKFOSA-N

物化性质

• 沸点：
  591.9±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)：
  1.0
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-galactopyranose-1,3,4,6-tetraacetate 在 吡啶 、 碳酸氢铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 174.0h， 生成 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose O-benzyl oxime ether
  参考文献：
  名称：

  Simpkins, Nigel S.; Stokes, Stephen; Whittle, Alan J., Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2471 - 2478

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose 在 盐酸 、 碳酸氢钠 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-galactopyranose-1,3,4,6-tetraacetate
  参考文献：
  名称：

  [EN] MAGNETIC LABELING OF BACTERIA
  [FR] MARQUAGE MAGNÉTIQUE DE BACTÉRIES

  摘要：

  本发明提供了一种新颖的方法，通过将细菌细胞与亲和配体接触，然后与磁性试剂接触，来实现对细菌细胞进行磁性标记。其中，亲和配体和磁性试剂包含可以相互反应形成共价键的生物正交反应基团。同时还描述了该方法的化合物、组合物、试剂盒和应用。

  公开号：

  WO2013187954A1

文献信息

• Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline
  作者：Gangliang Huang、Ya Chen

  DOI：10.2174/157018011796235220

  日期：2011.8.1

  The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  据报道，进行了双-N-乙酰-β-壳二糖基NAG（N-乙酰-D-葡萄糖胺）噻唑啉3的固相合成。首先合成了6-O-苄基NAG噻唑啉9、NHCbz三氯乙酸亚胺供体14和21，然后使用Wang树脂作为支持体进行固相合成。通过迭代糖基化反应、催化氢化、乙酰化和脱乙酰化，分别获得了目标双-N-乙酰-β-壳二糖基NAG噻唑啉3。
• Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl Allosamizoline
  作者：Gangliang Huang

  DOI：10.2174/157017811799304331

  日期：2011.11.1

  The solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline 2 was reported. After the 6-O-benzyl allosamizoline 16, NHCbz trichloroacetimidate donors 7, and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl allosamizoline 2 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  固相合成二-N-乙酰-β-壳二糖基别山黧豆碱2已见报道。在合成了6-O-苄基别山黧豆碱16、NHCbz三氯乙酰亚胺酯供体7和14之后，采用Wang树脂作为载体进行固相合成。目标二-N-乙酰-β-壳二糖基别山黧豆碱2通过反复糖基化反应、催化氢化、乙酰化和脱乙酰化分别获得。
• [EN] DETECTION OF MYCOBACTERIA<br/>[FR] DÉTECTION DE MYCOBACTÉRIES
  申请人：ISIS INNOVATION

  公开号：WO2011030160A1

  公开（公告）日：2011-03-17

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌种类存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标记，该探针分子可以被结核分枝杆菌所吸收，通过对标记的存在做出反应的探测器确定结核分枝杆菌的存在，可选地，在施加刺激后进行；适用的探针分子包括包含标记和底物的化合物，该标记可以被对标记的存在做出反应的探测器检测到，可选地，在施加刺激后进行，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点结合，从而能够与所选活性位点中的两个或更多氨基酸同时形成氢键，所选活性位点包括Arg 43、Trp 264、Ser126、His 262和Leu 42，或者抗原85A（Ag85A）或抗原85C（Ag85C）中对应的氨基酸，其中至少一个与Ser126形成氢键。
• Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
  作者：Chin-Sheng Chao、Min-Chun Chen、Shih-Che Lin、Kwok-Kong T. Mong

  DOI：10.1016/j.carres.2008.01.014

  日期：2008.4

  sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for D-galactose and L-fucose; (2) high yielding

  廉价且容易获得的磺酸，对甲苯磺酸和硫酸是通用且有效的催化剂，用于以良好的收率和在实际的时间范围内对多种碳水化合物底物进行过乙酰化。研究了磺酸催化游离糖乙酰化的三个吸引人的特征，包括：（1）抑制D-半乳糖和L-岩藻糖的呋喃糖基乙酸酯的形成；（2）在适当条件下高产率的唾液酸化学选择性乙酰化；（3）具有不同氨基保护功能的氨基糖过乙酰化。还描述了简单的一锅两步乙酰化-硫代糖苷化方法，用于快速合成对甲苯基过-O-乙酰基硫代糖苷。
• High-Efficiency Synthesis of Chitooligosaccharides
  作者：Gangliang Huang

  DOI：10.2174/157017811794557877

  日期：2011.1.1

  The solid-phase synthesis of chitooligosaccharides is described. After the NHCbz trichloroacetimidate donors 6 and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The illustrated tetra-Nacetyl- chitotetraose 1 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  固相合成壳寡糖的方法被描述如下：在合成NHCbz三氯乙亚胺酯供体6和14之后，使用Wang树脂作为载体进行固相合成。通过迭代的糖基化反应、催化氢化、乙酰化和脱乙酰化，分别得到了示例性的四乙酰化壳四糖1。