ALPHA-D-阿拉伯吡喃糖基叠氮化物 | 138892-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: ALPHA-D-阿拉伯吡喃糖基叠氮化物
• 英文名称: α-D-Arabinopyranosyl azide
• 英文别名: alpha-D-Arabinopyranosyl azide；(2S,3S,4R,5R)-2-azidooxane-3,4,5-triol
• CAS: 138892-04-3
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: WVWBURHISBVZHI-MBMOQRBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  ALPHA-D-阿拉伯吡喃糖基叠氮化物 在 镍 吡啶 、 氢气 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 (2S,3S,4R,5R)-2-(N-((R)-1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl)formamido)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reaktions on Carbohydrate Templates

  摘要：

  L-氨基酸衍生物在斯特克反应和乌吉反应中采用2,3,4-三-O-庚酰基-α-D-阿拉伯吡喃糖胺或2,3,4-三-O-庚酰基-β-L-岩藻糖吡喃糖胺作为手性辅助剂，立体选择性合成，产率高。

  DOI：

  10.1055/s-1991-26641
• 作为产物：
  描述：

  2,3,4-Tri-O-acetyl-α-D-arabinopyranosyl azide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到ALPHA-D-阿拉伯吡喃糖基叠氮化物
  参考文献：
  名称：

  Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reaktions on Carbohydrate Templates

  摘要：

  L-氨基酸衍生物在斯特克反应和乌吉反应中采用2,3,4-三-O-庚酰基-α-D-阿拉伯吡喃糖胺或2,3,4-三-O-庚酰基-β-L-岩藻糖吡喃糖胺作为手性辅助剂，立体选择性合成，产率高。

  DOI：

  10.1055/s-1991-26641

文献信息

• Epimerisation of Carbohydrates and Cyclitols, 17.1 Synthesis of Glycosyl Azides and N-Acetyl Glycosyl Amines of Rare Monosaccharides
  作者：Christian Hager、Ralf Miethchen、Helmut Reinke

  DOI：10.1055/s-2000-6250

  日期：——

  The glycosyl azides 1 (d-arabino), 3 (l-fuco), 5 (d-manno), and 7 (d-galacto) were epimerised in a one-pot procedure by heating with chloral/DCC/1,2-dichloroethane in good yields. The respective products, epimerised at the C-3 atom, have d-lyxo (2), l-gulo (4), d-altro (6), and d-gulo (8, 9) configuration. Compound 8, directly generated or obtained by deformylation of its 6-O-formyl derivative 9, was used as the key intermediate for further syntheses. Besides the acetylation of 8 to 10, and decarbamoylation to the 4,6-dihydroxy derivative 11, the latter 11 was acetylated to 12 and benzylated to 13. Moreover, the azide function of 8 was converted into an amino group using tributyltin hydride/AIBN or Staudinger conditions. The amino derivatives were isolated in the form of their N-acetyl derivatives 14 and 15, respectively. Finally, the dichloroethylidene (14) and the trichloroethylidene (15) groups were hydrodechlorinated forming the same ethylidene derivative 16. Crystal structures are given for the gulopyranoses 4 and 12.

  糖苷叠氮化物1（d-阿拉伯糖）、3（l-藤糖）、5（d-甘露糖）和7（d-半乳糖）通过与氯醛/DCC/1,2-二氯乙烷加热反应，在一步法中进行了表异构化，反应产率良好。相应的产物在C-3位发生了表异构化，分别具有d-氨基（2）、l-古洛（4）、d-阿尔特罗（6）和d-古洛（8、9）构型。化合物8是直接生成的或通过其6-O-甲酰衍生物9去甲酰化获得的，作为进一步合成的关键中间体。除了将8乙酰化生成10和去氨基化生成4,6-二羟基衍生物11外，后者11又乙酰化为12并苄基化为13。此外，8的叠氮功能团被转化为氨基，使用了三丁基锡氢化物/AIBN或斯陶丁格条件。氨基衍生物以其N-乙酰衍生物14和15的形式被分离。最后，二氯乙烯基（14）和三氯乙烯基（15）基团被去除氯化形成相同的乙烯基衍生物16。提供了古洛吡喃糖4和12的晶体结构。
• A Novel Class of Carbonic Anhydrase Inhibitors:  Glycoconjugate Benzene Sulfonamides Prepared by “Click-Tailing”
  作者：Brendan L. Wilkinson、Laurent F. Bornaghi、Todd A. Houston、Alessio Innocenti、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm060967z

  日期：2006.11.1

  Aryl and heteroaryl sulfonamides (ArSO2NH2) are therapeutically used to inhibit the catalytic activity of carbonic anhydrases (CAs). Using a "click- tail" approach a novel class of glycoconjugate benzene sulfonamides have been synthesized that contain diverse carbohydrate- triazole tails. These compounds were assessed for their ability to inhibit three human CA isozymes in vitro: cytosolic hCA I and hCA II and transmembrane, tumor- associated hCA IX. This isozyme has a minimal expression in normal tissue but is overexpressed in hypoxic tumors and its inhibition is a current approach toward new cancer therapies. The qualitative structure- activity for all derivatives demonstrated that the stereochemical diversity present within the carbohydrate tails effectively interrogated the CA active site topology, to generate several inhibitors that were potent and selective toward hCA IX, an important outcome in the quest for potential cancer therapy applications based on CA inhibition.
• Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reaktions on Carbohydrate Templates
  作者：Horst Kunz、Waldemar Pfrengle、Karola Rück、Wilfried Sager

  DOI：10.1055/s-1991-26641

  日期：——

  L-Amino acid derivatives are stereoselectively synthesized in high yield using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine or 2,3, 4-tri- O-pivaloyl-β-L-fucopyranosylamine as the chiral auxiliary in Strecker and Ugi reactions.

  L-氨基酸衍生物在斯特克反应和乌吉反应中采用2,3,4-三-O-庚酰基-α-D-阿拉伯吡喃糖胺或2,3,4-三-O-庚酰基-β-L-岩藻糖吡喃糖胺作为手性辅助剂，立体选择性合成，产率高。