(3R,4R)-6-cyano-3,4,5-tris(benzyloxy)-3,4-dihydro-2H-pyran | 138694-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R)-6-cyano-3,4,5-tris(benzyloxy)-3,4-dihydro-2H-pyran
• 英文别名: 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl cyanide；[(3R,4S,5S,6S)-4,5-dibenzoyloxy-6-cyanooxan-3-yl] benzoate
• CAS: 138694-36-7
• 化学式: C₂₇H₂₁NO₇
• 分子量: 471.466
• InChiKey: ZGWLZPXCCWSPTJ-KIHHCIJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R)-6-cyano-3,4,5-tris(benzyloxy)-3,4-dihydro-2H-pyran 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 以91%的产率得到5-(2',3',4'-tri-O-benzoyl-β-D-xylopyranosyl)tetrazole
  参考文献：
  名称：

  [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS
  [FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE

  摘要：

  公开号：

  WO2013061105A8
• 作为产物：
  描述：

  苯甲酸酐 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 63.0h， 生成 (3R,4R)-6-cyano-3,4,5-tris(benzyloxy)-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  未催化和分支酸变位酶催化的 5,6-二氢分支酸和 6-氧杂-5,6-二氢分支酸的克莱森重排

  摘要：

  描述了从 D-木糖合成 6-oxa-5,6-dihydrochorismic 酸 (4)。在 30 o C 下，5,6-二氢分支酸 (3) 和 4 在 D 2 O 中未催化的克莱森重排的半衰期分别为 49 000 和 1200 小时，而分支酸的半衰期为 15.6 小时（一）类似条件下

  DOI：

  10.1021/ja00030a039

文献信息

• Synthesis of 5-aryl-3-C-glycosyl- and unsymmetrical 3,5-diaryl-1,2,4-triazoles from alkylidene-amidrazones
  作者：Béla Szőcs、Éva Bokor、Katalin E. Szabó、Attila Kiss-Szikszai、Marietta Tóth、László Somsák

  DOI：10.1039/c5ra05702g

  日期：——

  Bromination of the so obtained compounds by NBS gave hydrazonoyl bromide type derivatives which were ring closed to 3-C-glycosyl-5-substituted-1,2,4-triazoles in pyridine or by NH4OAc in AcOH. Under the same conditions O-perbenzoylated N1-arylidene-C-(β-D-glucopyranosyl)-formamidrazones gave the expected 1,2,4-triazoles as minor products only. N1-Arylidene-arenecarboxamidrazones were also transformed

  在具有多种生物活性的1,2,4-三唑衍生物中，3 - C-吡喃葡萄糖基-5-取代的1,2,4-三唑属于糖原磷酸化酶的最有效抑制剂，因此是潜在的降糖药。在寻找用于这类化合物的新的合成方法中，研究了N 1-亚烷基羧酰胺dra的氧化性闭环。在NaH 2 PO 2存在下，通过Raney-Ni®还原反应，由相应的糖基氰化物和酰氨基prepared酰胺制备O-酰化的N 1-（β- D-甘氨酸金烷基糖基亚甲基）-芳族羧酰胺基酮。通过NBS对如此获得的化合物进行溴化得到了酰肼基溴化物型衍生物，其在吡啶中或在AcOH中通过NH 4 OAc与3- C-糖基-5-取代-1,2,4-三唑闭环。在相同条件下ø -perbenzoylated Ñ 1 -arylidene- Ç - （β- d吡喃葡萄糖基）-formamidrazones给出预期的-1,2,4-三唑作为只有轻微的产品。N 1-亚芳基-亚芳基甲酰胺还与NBS
• Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media
  作者：Anup Kumar Misra、Éva Bokor、Sándor Kun、Evelin Bolyog-Nagy、Ágnes Kathó、Ferenc Joó、László Somsák

  DOI：10.1016/j.tetlet.2015.09.040

  日期：2015.10

  [RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water–N-methylpyrrolidone solvent mixtures at 105 °C. O-Acetyl, O-benzoyl, and O-benzyl protecting groups, anomeric bromide and azide substituents as well as double bonds were shown to be compatible with these

  将[RuCl 2（DMSO）4 ]中的存在Ñ -benzylated 1,3,5-三氮杂-7-磷有效地催化糖基氰化物的水合为相应的甲酰胺衍生物在水或水ñ在105甲基吡咯烷酮溶剂混合物℃。已表明O-乙酰基，O-苯甲酰基和O-苄基保护基，端基溴和叠氮化物取代基以及双键与这些反应条件相容。
• Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase
  作者：László Somsák、Éva Bokor、Beáta Czibere、Katalin Czifrák、Csenge Koppány、László Kulcsár、Sándor Kun、Enikő Szilágyi、Marietta Tóth、Tibor Docsa、Pál Gergely

  DOI：10.1016/j.carres.2014.05.020

  日期：2014.11

  New derivatives of D-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(beta-D-xylopyranosyl) benzimidazole and 3-substituted-5-(beta-D-xylopyranosyl)1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated b-D-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding beta-D-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated beta-D-xylopyranosyl-thiohydroximates prepared from 1-thio-beta-D-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(beta-D-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only. (C) 2014 Elsevier Ltd. All rights reserved.
• One-pot transformation of glycopyranosylcyanides to N-(t-butoxycarbonyl)methylamines
  作者：Dirk H Lenz、Gillian E Norris、Carol M Taylor、George C Slim

  DOI：10.1016/s0040-4039(01)00804-8

  日期：2001.7

  Protected glycopyranosylcyanides were transformed into the corresponding N-tert-butoxycarbonyl-glycopyranosyl methylamines in a one-pot transformation in high yields. This general method is applicable to glycopyranosylcyanides bearing common O- and N-protecting groups frequently used in carbohydrate chemistry. (C) 2001 Published by Elsevier Science Ltd.