3-aminomethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 38088-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-aminomethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-6-(aminomethyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 38088-37-8
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: SRUQFMDAROAOHF-YANYRWCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-aminomethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 苄基三乙基氯化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.83h， 生成 (3S)-1,2:5,6-di-O-isopropylidene-spiro(3-deoxy-α-D-glucofuranose-3,5'-oxazolidin)-2'-one
  参考文献：
  名称：

  A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate

  摘要：

  A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.04.008
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose 在 palladium on activated charcoal 、 水 、 氢气 、 乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 生成 3-aminomethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  由异脲和葡糖呋喃糖酶合成单体亚甲基连接的1,2,3-三唑糖缀合物

  摘要：

  碳水化合物-三唑共轭物证明自己是有价值的酶活性调节剂。对非平凡缀合物的最新研究表明，该键不是在糖的糖苷或末端碳上而是在C-3位置形成的，显示出这种结构作为各种糖苷酶和半乳糖凝集素的配体的潜力。在这里，我们报道了受保护的3- C-（三唑基甲基）-取代的葡萄糖-和同种共轭物的合成。非对映体叠氮化物是由常见的中间体3-deoxy-1,2：5,6 -di - O -isopropylidene-3-oxo-α-D-alalfuranose合成的，并用于Cu催化的叠氮化物-炔烃环加成反应（CuAAC）与商业炔烃。在不同的催化条件下，环加成反应的产率良好至优异。

  DOI：

  10.1007/s10593-015-1791-5

文献信息

• Novel 3-C-aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis
  作者：Māris Turks、Evija Rolava、Dmitrijs Stepanovs、Anatoly Mishnev、Dean Marković

  DOI：10.1016/j.tetasy.2015.07.003

  日期：2015.9

  Both 1,2:5,6-di-O-isopropylidene- and 1,2:5,6-di-O-cyclohexylidene-alpha-D-glucofuranose-derived ketones provided the corresponding branched 3-C-nitromethyl-congeners in the Henry reaction with nitromethane anion. Reduction of the nitro moiety followed by derivatization with iso(thio)cyanates gave 3-C-aminomethyl-hexofuranose-derived (thio)ureas. The relative configuration of the products in each series was unambiguously established by X-ray analysis. The title products were shown to act as organocatalysts in Friedel Crafts alkylations of indoles with beta-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones. (C) 2015 Elsevier Ltd. All rights reserved.
• KUSZMANN, JANOS;MARTON-MERESZ, MAGDOLNA;JERKOVICH, GYULA, CARBOHYDR. RES., 175,(1988) N 2, 249-264
  作者：KUSZMANN, JANOS、MARTON-MERESZ, MAGDOLNA、JERKOVICH, GYULA

  DOI：——

  日期：——