3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranoside | 16848-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranoside
• 英文别名: 1,2:5,6-di-O-isopropylidene-3-amino-3-deoxy-α-D-allofuranose；3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-Amino-3-desoxy-1,2:5,6-di-O-isopropyliden-α-D-allofuranose；(3aR,5S,6R,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-amine
• CAS: 16848-19-4；24384-84-7；71165-01-0；71187-80-9；73881-34-2；91067-83-3
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: SHQAHGPRANRAGI-VAPHQMJDSA-N

物化性质

• 熔点：
  89-91 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  323.5±42.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranoside 、 2,2'-联吡啶-3,3'-二羧酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到N,N'-bis-(3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-1-yl)-2,2'-bipyridine-3,3'-carboxamide
  参考文献：
  名称：

  2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination

  摘要：

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.050
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-triflyl-α-D-glucofuranose 在 ammonium hydroxide 、 1,2-二氯乙烷 作用下， 反应 48.0h， 以58%的产率得到3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranoside
  参考文献：
  名称：

  氨基脱氧糖的新有效途径

  摘要：

  描述了一种温和且方便的氨基脱氧糖合成方法，包括部分保护的碳水化合物与三氟甲磺酸酐的酯化反应以及所得三氟甲磺酸盐与氨的反应。不存在在碳水化合物系统中置换反应中遇到的某些困难。

  DOI：

  10.1039/c39840001530

文献信息

• Arynes in the Monoarylation of Unprotected Carbohydrate Amines
  作者：Kumar Bhaskar Pal、Mukul Mahanti、Ulf J. Nilsson

  DOI：10.1021/acs.orglett.7b03741

  日期：2018.2.2

  A CsF-mediated method has been developed for the N-arylation of amino sugars that affords good to excellent yields of arylated products under mild conditions involving the in situ generation of arynes. The reaction conditions tolerate a variety of common carbohydrate protecting groups and also performs exceptionally well on unprotected amino sugar derivatives. The reactions are scalable in moderate

  已经开发出用于氨基糖的N-芳基化的CsF介导的方法，其在涉及原位生成芳烃的温和条件下提供良好至优异的芳基化产物收率。反应条件可耐受多种常见的碳水化合物保护基，并且在未保护的氨基糖衍生物上也表现出色。反应范围宽广，可以中等至良好的收率进行扩展。
• Palladium-Catalyzed Intramolecular Aryl Amination Reaction: An Expeditious Approach to the Synthesis of Chiral Benzodiazocine Derivatives
  作者：Nirmal Das Adhikary、Partha Chattopadhyay

  DOI：10.1002/ejoc.200901472

  日期：2010.3

  electron-rich aryl halide substrates have been aminated by the intramolecular pathway in good yield using different sugar-derived amines as well as benzylamine. The method is capable of furnishing benzodiazocines in chiral form besides dibenzodiazocine derivatives of potential biological interest.

  已经开发了一种钯催化的芳基溴化物和碘化物分子内胺化方法，采用不同的大体积联芳基膦作为配体，甲苯作为溶剂。各种富含电子的芳基卤化物底物已使用不同的糖衍生胺和苄胺通过分子内途径以良好的产率胺化。除了具有潜在生物学意义的二苯并二氮唑衍生物外，该方法还能够提供手性形式的苯并二氮唑。
• A novel, simple, chemoselective and practical protocol for the reduction of azides using In/NH4Cl
  作者：G.Vidyasagar Reddy、G.Venkat Rao、D.S. Iyengar

  DOI：10.1016/s0040-4039(99)00614-0

  日期：1999.5

  A simple, mild and efficient method for the reduction of azides to amines using In / NH4Cl is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
  作者：Aurélie Assalit、Thierry Billard、Stéphane Chambert、Bernard R. Langlois、Yves Queneau、Diane Coe

  DOI：10.1016/j.tetasy.2009.02.050

  日期：2009.3

  A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2'-bipyridine-3,3'-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.
• A new efficient access to aminodeoxy sugars
  作者：Abdul Malik、Nighat Afza、Michael Roosz、Wolfgang Voelter

  DOI：10.1039/c39840001530

  日期：——

  A mild and convenient synthesis of aminodeoxy sugars is described, involving the esterification of partially protected carbohydrates with trifluoromethanesulphonic anhydride and the reaction of the resulting trifluoromethanesulphonates with ammonia; the difficulties which sometines encountered in displacement reactions in carbohydrate systems are absent.

  描述了一种温和且方便的氨基脱氧糖合成方法，包括部分保护的碳水化合物与三氟甲磺酸酐的酯化反应以及所得三氟甲磺酸盐与氨的反应。不存在在碳水化合物系统中置换反应中遇到的某些困难。