1,2,3-tri-O-acetyl-5-deoxy-5-isothiocyanato-D-xylofuranose | 260544-64-7

• 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: 1,2,3-tri-O-acetyl-5-deoxy-5-isothiocyanato-D-xylofuranose
• 英文别名: [(2R,3S,4R)-4,5-diacetyloxy-2-(isothiocyanatomethyl)oxolan-3-yl] acetate
• CAS: 260544-64-7
• 化学式: C₁₂H₁₅NO₇S
• 分子量: 317.32
• InChiKey: ZTFSFDHTJFVHOU-FBTJUVTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3-tri-O-acetyl-5-deoxy-5-isothiocyanato-D-xylofuranose 在 吡啶 、 sodium methylate 作用下， 生成 (2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-N-(N'-phenylthiocarbamoyl)piperidine
  参考文献：
  名称：

  Polyhydroxylated N-(thio)carbamoyl piperidines: nojirimycin-type glycomimetics with controlled anomeric configuration

  摘要：

  N-(Thio)carbamoyl D-xylo-nojirimycin derivatives have been prepared by intramolecular rearrangement of sugar thiourea precursors under basic conditions. The stereochemistry at the aminoketal stereocentre is under stereoelectronic control, with the diastereomer having the pseudoanomeric group in axial orientation being obtained in all cases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00462-0
• 作为产物：
  描述：

  5-azido-5-deoxy-α,β-D-xylose 在 吡啶 、 焦磷酸硫胺素 作用下， 生成 1,2,3-tri-O-acetyl-5-deoxy-5-isothiocyanato-D-xylofuranose
  参考文献：
  名称：

  Polyhydroxylated N-(thio)carbamoyl piperidines: nojirimycin-type glycomimetics with controlled anomeric configuration

  摘要：

  N-(Thio)carbamoyl D-xylo-nojirimycin derivatives have been prepared by intramolecular rearrangement of sugar thiourea precursors under basic conditions. The stereochemistry at the aminoketal stereocentre is under stereoelectronic control, with the diastereomer having the pseudoanomeric group in axial orientation being obtained in all cases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00462-0

文献信息

• Synthesis and Evaluation of Calystegine B₂ Analogues as Glycosidase Inhibitors
  作者：M. Isabel García-Moreno、Juan M. Benito、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/jo015639f

  日期：2001.11.1

  bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect. A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver beta-glucosidase was observed for 6-oxacalystegine B(2) analogues

  提出了一种实用的多羟基化的6-氧杂-正-烷烷类化合物，由5-脱氧-5-硫脲基和5-脲基-L-呋喃丹糖前体结合了calystegine B（2）的基本结构特征。该方法依赖于假酰胺型氮原子（硫脲，尿素和氨基甲酸酯）对单糖的掩蔽醛基进行亲核加成的能力。产生的半胱氨酸功能性可以进一步进行原位分子内糖苷化以产生双环氨基缩醛化合物，整个过程受到异头作用的促进。已经制备了一系列在氮原子上带有不同取代基的衍生物，并与木糖苷嘧啶型哌啶类似物相比，针对几种糖苷酶进行了筛选。有趣的是 强烈和高度特异性抑制牛肝β-葡糖苷酶的6-氧杂天冬氨酸B（2）类似物并入芳香假糖苷基团。基于这些数据，针对该糖模拟物家族提出了一种1-氮杂糖抑制模式。
• One-step synthesis of non-anomeric sugar isothiocyanates from sugar azides
  作者：M.Isabel Garcı́a-Moreno、Paula Dı́az-Pérez、Juan M. Benito、Carmen Ortiz Mellet、Jacques Defaye、José M. Garcı́a Fernández

  DOI：10.1016/s0008-6215(02)00273-2

  日期：2002.11

  yield. No products arising from O --> N acyl migration or formation of dimeric carbodiimides were observed. Interestingly, a polymer-supported triarylphosphine can advantageously replace triphenylphosphine, thus limiting the purification step to a simple filtration process. The reaction also allows the preparation of 5-deoxy-5-isothiocyanato sugars, a hitherto unknown class of compounds, from the corresponding

  初级叠氮基脱氧糖与三苯基膦-二硫化碳的串联Staudinger-aza-Wittig反应以高收率提供了相应的初级脱氧异硫氰酸氰基糖。没有观察到由于O-> N酰基迁移或形成二聚碳二亚胺而产生的产物。有趣的是，聚合物负载的三芳基膦可以有利地代替三苯基膦，因此将纯化步骤限制为简单的过滤过程。该反应还允许从相应的叠氮化物前体制备5-脱氧-5-异硫氰酸根合糖，这是迄今未知的一类化合物。在这些反应条件下，在内环碳原子上带有叠氮基的仲糖叠氮化物提供了低得多的异硫氰化产率。