Acetic acid (2R,3S)-2-acetoxymethyl-6-azido-3,6-dihydro-2H-pyran-3-yl ester | 471923-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: Acetic acid (2R,3S)-2-acetoxymethyl-6-azido-3,6-dihydro-2H-pyran-3-yl ester
• 英文别名: [(2R,3S)-3-acetyloxy-6-azido-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 471923-29-2
• 化学式: C₁₀H₁₃N₃O₅
• 分子量: 255.23
• InChiKey: UYMVJHPTGITZSS-QIIDTADFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-yn-1-yl 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylate 、 Acetic acid (2R,3S)-2-acetoxymethyl-6-azido-3,6-dihydro-2H-pyran-3-yl ester 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以90%的产率得到(1-((5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl 2-((1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl) acrylate
  参考文献：
  名称：

  Synthesis of artemisinic acid derived glycoconjugates and their anticancer studies

  摘要：

  使用点击反应合成了24种青蒿酸糖基共轭杂合物，并对其针对MCF7细胞系的抗癌活性进行了评估。

  DOI：

  10.1039/d0ob00216j
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 叠氮基三甲基硅烷 、 氯化锆(IV) 作用下， 以 乙腈 为溶剂， 反应 0.13h， 以86%的产率得到Acetic acid (2R,3S)-2-acetoxymethyl-6-azido-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  ZrCl₄-Catalyzed Efficient Ferrier Glycosylation: A Facile Synthesis of Pseudoglycals

  摘要：

  三-O-乙酰基-d-葡糖醛与硅烷亲核试剂、醇和硫醇的反应在少量四氯化锆的催化作用下有效促进，生成相应的伪葡糖醛，经过Ferrier重排反应。

  DOI：

  10.1055/s-2004-815974

文献信息

• Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me₃SiN₃. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar
  作者：Ande Chennaiah、Srijita Bhowmick、Yashwant D. Vankar

  DOI：10.1039/c7ra08637g

  日期：——

  Glycals were found to react with a reagent system comprising of phenyliodine bis(trifluoroacetate) (PIFA) and Me3SiN3 in the presence of TMSOTf as a catalyst to form the corresponding vicinal 1,2-diazides. On the other hand, they reacted with another reagent system phenyliodine diacetate (PIDA) and Me3SiN3, also in the presence of TMSOTf as a catalyst, to lead to the corresponding vicinal 1,2-azidoacetates

  发现乙二醇在TMSOTf作为催化剂存在下与包含苯基碘双（三氟乙酸盐）（PIFA）和Me 3 SiN 3的试剂系统反应形成相应的邻位1,2-二叠氮化物。另一方面，它们也在TMSOTf作为催化剂的情况下与另一种试剂体系苯乙酸二乙酸苯酯（PIDA）和Me 3 SiN 3反应，生成相应的邻位1,2-叠氮基乙酸酯。这些叠氮基衍生物被转化为许多2-叠氮基-N-糖肽，伪三糖和哌啶三醇衍生物亚氨基糖。
• A tandem Ferrier and Click reaction: a facile synthesis of triazolyl-2,3-dideoxypyranosides
  作者：J.S. Yadav、B.V. Subba Reddy、D. Narasimha Chary、Ch. Suresh Reddy

  DOI：10.1016/j.tetlet.2008.02.052

  日期：2008.4

  smooth coupling with alkynes under neutral conditions by means of ‘Click reactions’ to furnish 1,2,3-triazole-linked glycoconjugates in high yields and with moderate stereoselectivity. The method provides a convenient route to prepare glycoconjugates from glucals, trimethylsilyl azide, and alkynes via a three component reaction.

  由葡萄糖和三甲基甲硅烷基叠氮化物通过Ferrier重排原位制备的叠氮化物糖基在中性条件下通过“点击反应”与炔烃进行平滑偶联，从而以高收率和适度的立体选择性提供1,2,3-三唑连接的糖缀合物。该方法提供了通过三组分反应从葡糖，三甲基甲硅烷基叠氮化物和炔烃制备糖缀合物的便利途径。
• Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-<i>C</i>-glycoside
  作者：Alafia A Ansari、Y Suman Reddy、Yashwant D Vankar

  DOI：10.3762/bjoc.10.27

  日期：——

  A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles. The obtained C-allyl glycoside has been utilized for the synthesis of a orthogonally protected 2-a

  通过使用硝酸铈铵对糖类进行碳-费里叶重排，以高选择性获得中等至良好收率的产物。该方法的多功能性已通过将其应用于不同保护的糖类和使用几种亲核试剂来证明。获得的 C-烯丙基糖苷已用于合成正交保护的 2-氨基-2-脱氧-C-糖苷。
• Sc(OTf)3-catalyzed C-glycosidation of glycals: a facile synthesis of allyl glycosides, glycosyl cyanides and glycosyl azides
  作者：J.S Yadav、B.V.Subba Reddy、Pratap K Chand

  DOI：10.1016/s0040-4039(01)00629-3

  日期：2001.6

  The treatment of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in the presence of catalytic amounts of Sc(OTf)(3) gave the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high cl-selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tris(pentafluorophenyl)borane catalyzed Ferrier azaglycosylation with sulfonamides and carbamates
  作者：S. Chandrasekhar、Ch. Raji Reddy、G. Chandrashekar

  DOI：10.1016/j.tetlet.2004.06.120

  日期：2004.8

  The reaction of tri-O-acetyl-D-glucal with different nitrogen nucleophiles was effectively promoted by a catalytic amount of tris(pentafluorophenyl)borane for the first time in acetonitrile at room temperature to produce a variety of azapseudoglycals via Ferrier rearrangement in good yields and preferential anomeric selectivity. (C) 2004 Published by Elsevier Ltd.