3-C-aminomethyl-1,2:5,6-di-O-isoprolylidene-α-D-allofuranose | 38088-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-aminomethyl-1,2:5,6-di-O-isoprolylidene-α-D-allofuranose
• 英文别名: 3-C-aminomethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• CAS: 38088-36-7
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: SRUQFMDAROAOHF-OAZVDXGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 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：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-C-aminomethyl-1,2:5,6-di-O-isoprolylidene-α-D-allofuranose 在 triflic azide 、 碳酸氢钠 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 以77%的产率得到(3R)-3-azidomethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  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
• 作为产物：
  描述：

  3-C-cyano-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以59%的产率得到3-C-aminomethyl-1,2:5,6-di-O-isoprolylidene-α-D-allofuranose
  参考文献：
  名称：

  立体控制合成（5 + 5），（5 + 6）和（6 + 6）3-螺伪核苷

  摘要：

  已经从六呋喃糖-3-基糖开始制备了3-螺伪假核苷，其中杂环碱基是五元（恶唑烷，咪唑烷，硫代乙内酰脲）或六元（全氢恶嗪）杂环。该方法产生了良好的产率，并且是完全立体选择性的。关键中间体是糖异（硫）氰酸酯。

  DOI：

  10.1016/j.tet.2009.03.038

文献信息

• Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly
  作者：Vitālijs Rjabovs、Pāvels Ostrovskis、Daniels Posevins、Gļebs Kiseļovs、Viktors Kumpiņš、Anatoly Mishnev、Māris Turks

  DOI：10.1002/ejoc.201500695

  日期：2015.9

  Synthetic approaches to new N-protected γ- and δ-furanoid sugar amino acids (SAAs) or tetrahydrofuran amino acids were developed. SAAs have emerged as valuable building blocks for the syntheses of peptide mimetics, so-called carbopeptoids. 3-C-Substituted 1,2-O-isopropylidene-α-D-allofuranose derivatives were used as starting materials. The designed SAAs contain either cis- or trans-oriented C(3)-aminomethyl

  开发了新的 N 保护的 γ-和 δ-呋喃糖氨基酸 (SAA) 或四氢呋喃氨基酸的合成方法。SAA 已成为合成肽模拟物（即所谓的类肽）的重要组成部分。3-C-取代的1,2-O-异亚丙基-α-D-异呋喃糖衍生物用作原料。设计的 SAA 含有顺式或反式 C(3)-氨基甲基和 C(4)-或 C(5)-羧酸官能团连接到 1,2-O-异亚丙基呋喃核，从而提供不同的空间安排。合成衍生自 γ-SAA 和 δ-SAA 的短链均聚物作为探索新类碳肽的第一步。
• Synthesis and glycosidase inhibition evaluation of (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol
  作者：En Zhang、Peng-Yan Bai、Wei Sun、Shang Wang、Ming-Ming Wang、Shuai-Min Xu、Hong-Min Liu

  DOI：10.1016/j.carres.2016.08.003

  日期：2016.11

  isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50 > 100 muM).

  使用一锅还原环化作为关键步骤从市售d-葡萄糖中获得了一种新的氮杂糖（3S，4S）-3-（（R）-1,2-二羟乙基）吡咯烷-3,4-二醇（1） 。分十步获得目标产物，即亚氨基糖异构体，总产率为24.3％。在该合成中仅需要三个柱色谱纯化。研究了靶分子作为糖苷酶抑制剂的生物活性，但对四种糖苷酶的抑制活性不好（IC50> 100μM）。
• Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins
  作者：Jevgeņija Mackeviča、Pāvels Ostrovskis、Hakon Leffler、Ulf J. Nilsson、Vita Rudovica、Arturs Viksna、Sergey Belyakov、Māris Turks

  DOI：10.3998/ark.5550190.p008.402

  日期：——

  treatment with EDTA and Na2S followed by chromatographic purification. Acidic hydrolysis of the acetonide protecting groups provided water soluble galactohybrids that were tested for their affinity towards galectin-1 and galectin-3. The trimeric galactohybrid exhibited a 160-fold preference for galectin-3 binding with K-d 50 mu M. One of the obtained disaccharides was characterized by X-ray analysis.

  这里描述了新型半乳糖-1,2,3-三唑缀合物的合成。通过铜催化的叠氮化物-炔烃 1,3-偶极环加成反应，从 3-叠氮基-3-脱氧-1,2: 5,6-二-O-异亚丙基-α-D-呋喃半乳糖获得标题化合物。已证明呈异亚丙基保护形式的标题化合物倾向于螯合铜。通过依次用 EDTA 和 Na2S 处理，然后进行色谱纯化，可以将铜含量降低到 10 ppm。丙酮化物保护基团的酸性水解提供了水溶性半乳糖杂化物，测试了它们对半乳糖凝集素-1 和半乳糖凝集素-3 的亲和力。三聚半乳糖杂种对半乳糖凝集素 3 与 Kd 50 μ M 的结合表现出 160 倍的偏好。获得的二糖之一通过 X 射线分析进行了表征。（较少的）
• A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate
  作者：Māris Turks、Vitalijs Rodins、Evija Rolava、Pāvels Ostrovskis、Sergey Belyakov

  DOI：10.1016/j.carres.2013.04.008

  日期：2013.6

  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.
• 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.