5-azido-5-deoxy-α,β-D-xylose | 4768-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-α,β-D-xylose
• 英文别名: (3R,4R,5R)-5-(azidomethyl)oxolane-2,3,4-triol
• CAS: 4768-70-1
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: FPNYNARZVKFPAC-IOVATXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  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-(3-phenylthioureido)-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
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 sodium azide 、 Dowex 50 W (H⁺) 、 水 、 尿素 作用下， 以 水 为溶剂， 反应 20.75h， 生成 5-azido-5-deoxy-α,β-D-xylose
  参考文献：
  名称：

  Synthesis of 5-Amino-5-deoxypentonolactams

  摘要：

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。

  DOI：

  10.1135/cccc19961027

文献信息

• Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy
  作者：Manuel Zoidl、Bernhard Müller、Ana Torvisco、Christina Tysoe、Mohamed Benazza、Aloysius Siriwardena、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2014.03.069

  日期：2014.6

  A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-D-xylose and -D-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-D-idurono nitrile and 2,6-didesoxy-2,6-imino-D-glycero-D-ido-heptononitrile. (C) 2014 Published by Elsevier Ltd.
• Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives
  作者：Philipp Hadwiger、Peter Mayr、Andreas Tauss、Arnold E Stütz、Bernd Nidetzky

  DOI：10.1016/s0960-894x(99)00255-3

  日期：1999.6

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Polyhydroxylated N-(thio)carbamoyl piperidines: nojirimycin-type glycomimetics with controlled anomeric configuration
  作者：M.Isabel Garcı́a-Moreno、Carmen Ortiz Mellet、José M Garcı́a Fernández

  DOI：10.1016/s0957-4166(99)00462-0

  日期：1999.11

  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.
• Synthesis of 5-Amino-5-deoxypentonolactams
  作者：Karel Kefurt、Zdeňka Kefurtová、Věra Marková、Karla Slívová

  DOI：10.1135/cccc19961027

  日期：——

  5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (15) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (17) were obtained from 4 and 10, respectively. The derivatives 4, 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-pentofuranoses 6, 11, 18, 19, 5-azido-5-deoxy-D-pentonolactones 7, 12, 20, 21 and 5-amino-5-deoxy-D-pentonolactams 8, 13, 22, 23.

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。