α-D-mannopyranosyluronic acid azide | 562847-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-mannopyranosyluronic acid azide
• 英文别名: 1-deoxy-1-azido-α-D-mannohexopranosiduronic acid；(2S,3S,4S,5S,6S)-6-azido-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 562847-46-5
• 化学式: C₆H₉N₃O₆
• 分子量: 219.154
• InChiKey: HFKUSYWEILNCQU-RCBNBJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  α-D-mannopyranosyluronic acid azide 在 α(1-3)galactosyl-transferase 、 人体β-1,4-半乳糖转移酶I重组体来源于酿酒酵母 苯磺酰胺 、 sodium methylate 、 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 、 manganese(ll) chloride 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 128.0h， 生成 8-methoxycarbonyloctyl α-D-galactopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-2-deoxy-2-(1-deoxy-1-azido-α-D-mannohexopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors

  摘要：

  A series of D- and L-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These 'disaccharides'. in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for beta (1-4)-galactosyl-transferase and alpha (1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates. despite the far reaching, alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00086-4
• 作为产物：
  描述：

  ALPHA-D-甘露糖基叠氮化物 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 calcium hypochlorite 、 potassium bromide 作用下， 以 碳酸氢钠 为溶剂， 反应 48.0h， 以10%的产率得到α-D-mannopyranosyluronic acid azide
  参考文献：
  名称：

  合成吡喃葡萄糖基尿酸叠氮化物的一般方法

  摘要：

  首先将衍生自单糖和二糖的过-O-乙酰化D-甘露聚糖转化为糖基碘，然后与叠氮化物源反应，以在脱乙酰基反应后实现立体选择性合成β-D-糖基叠氮化物。单糖的低温（4摄氏度）TEMPO氧化提供了相应的糖醛酸，其被纯化为游离酸。乳糖基和纤维二糖叠氮化物的氧化导致二酸形成。然而，4'，6'-O-亚苄基保护能够选择性氧化C-6羟基。还制备了2-乙酰胺基-2-脱氧-D-甘露糖基叠氮化物，并将其转化为糖醛酸，从而完成了文库的合成。

  DOI：

  10.1016/s0008-6215(03)00042-9

文献信息

• Synthesis of methyl (d-glycopyranosyl azide) uronates
  作者：Zoltán Györgydeák、Joachim Thiem

  DOI：10.1016/0008-6215(94)00313-5

  日期：1995.3

  Abstract Sodium hypochlorite oxidation catalysed by 2,2,6,6,-tetramethylpiperidine 1-oxide (TEMPO) is shown to be a mild and efficient approach to the title uronates. In the gluco, galacto, allo , and 2-acetamido-2-deoxy- gluco series, the corresponding β- or α- and β-glycosyl azides could be smoothly oxidised and alternative preparations are compared to this access.

  摘要显示了由2,2,6,6，-四甲基哌啶1-氧化物（TEMPO）催化的次氯酸钠氧化是一种温和而有效的标题尿酸盐的方法。在葡萄糖，半乳糖，同素和2-乙酰氨基-2-脱氧-葡萄糖系列中，相应的β-或α-和β-糖基叠氮化物可以被平滑地氧化，并将替代制剂与这种方法进行比较。
• General methods for the synthesis of glycopyranosyluronic acid azides
  作者：Laiqiang Ying、Jacquelyn Gervay-Hague

  DOI：10.1016/s0008-6215(03)00042-9

  日期：2003.4

  converted to glycosyl iodides and subsequently reacted with an azide source to achieve the stereoselective synthesis of beta-D-glycosyl azides after deacetylation. Low-temperature (4 degrees C) TEMPO oxidation of the monosaccharides provided the corresponding uronic acids, which were purified as the free acids. Oxidation of the lactosyl- and cellobiosyl azides resulted in diacid formation. However, 4',6'-O-benzylidene

  首先将衍生自单糖和二糖的过-O-乙酰化D-甘露聚糖转化为糖基碘，然后与叠氮化物源反应，以在脱乙酰基反应后实现立体选择性合成β-D-糖基叠氮化物。单糖的低温（4摄氏度）TEMPO氧化提供了相应的糖醛酸，其被纯化为游离酸。乳糖基和纤维二糖叠氮化物的氧化导致二酸形成。然而，4'，6'-O-亚苄基保护能够选择性氧化C-6羟基。还制备了2-乙酰胺基-2-脱氧-D-甘露糖基叠氮化物，并将其转化为糖醛酸，从而完成了文库的合成。
• Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors
  作者：Oliver Schwardt、Gabi Baisch、Reinhold Öhrlein

  DOI：10.1016/s0968-0896(01)00086-4

  日期：2001.7

  A series of D- and L-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These 'disaccharides'. in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for beta (1-4)-galactosyl-transferase and alpha (1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates. despite the far reaching, alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides. (C) 2001 Elsevier Science Ltd. All rights reserved.