(1'S,2'R,3'R,4'R)-5,6-dimethyl-2-[1',2',3',4',5'-pentahydroxypentyl]benzimidazole | 84986-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (1'S,2'R,3'R,4'R)-5,6-dimethyl-2-[1',2',3',4',5'-pentahydroxypentyl]benzimidazole
• 英文别名: (1S,2R,3R,4R)-2-(1,2,3,4,5-pentahydroxypentyl)-1H-5,6-dimethylbenzimidazole；2-(D-gluco-pentitol-1-yl)-5,6-dimethylbenzimidazole；5,6-dimethyl-2-(D-gluco-pentitol-1-yl)benzimidazole
• CAS: 84986-15-2
• 化学式: C₁₄H₂₀N₂O₅
• 分子量: 296.323
• InChiKey: OVHZYNNOYDWSOP-FVCCEPFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129.83
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1'S,2'R,3'R,4'R)-5,6-dimethyl-2-[1',2',3',4',5'-pentahydroxypentyl]benzimidazole 、 乙酸酐 在 吡啶 作用下， 以1.08 g的产率得到5,6-dimethyl-2-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)benzimidazole
  参考文献：
  名称：

  MAOS ofD‐Gluconic Acid,D‐Glucono‐1,4‐ and 1,5‐Lactones, Esters, Hydrazides, and Benzimidazoles Thereof

  摘要：

  Microwave-assisted organic synthesis (MAOS) of D-gluconic acid can be efficiently done by oxidation of D- glucose with bromine water, upon irradiation with microwave ( MW). It was also used for the conversion of D-gluconic acid to ethyl D-gluconate, D-glucono-1,4- and 1,5-lactones, gluconyl hydrazide, and gluconyl phenylhydrazide in yields comparable to those obtained by conventional methods, but in much shorter times. A convenient microwave- mediated condensation of D- gluconic acid with o-phenylenediamines provided the respective acyclonucleoside benzimidazole in short time and good yield.[GRAPHICS]

  DOI：

  10.1080/07328300701540258
• 作为产物：
  描述：

  5,6-dimethyl-2-(1,2,3,4,5-penta-O-acetyl-D-gluco-pentitol-1-yl)benzimidazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(1'S,2'R,3'R,4'R)-5,6-dimethyl-2-[1',2',3',4',5'-pentahydroxypentyl]benzimidazole
  参考文献：
  名称：

  MAOS ofD‐Gluconic Acid,D‐Glucono‐1,4‐ and 1,5‐Lactones, Esters, Hydrazides, and Benzimidazoles Thereof

  摘要：

  Microwave-assisted organic synthesis (MAOS) of D-gluconic acid can be efficiently done by oxidation of D- glucose with bromine water, upon irradiation with microwave ( MW). It was also used for the conversion of D-gluconic acid to ethyl D-gluconate, D-glucono-1,4- and 1,5-lactones, gluconyl hydrazide, and gluconyl phenylhydrazide in yields comparable to those obtained by conventional methods, but in much shorter times. A convenient microwave- mediated condensation of D- gluconic acid with o-phenylenediamines provided the respective acyclonucleoside benzimidazole in short time and good yield.[GRAPHICS]

  DOI：

  10.1080/07328300701540258

文献信息

• Using Molecular Iodine in Direct Oxidative Condensation of Aldoses with Diamines: An Improved Synthesis of Aldo-benzimidazoles and Aldo-naphthimidazoles for Carbohydrate Analysis
  作者：Chunchi Lin、Po-Ting Lai、Sylvain Kuo-Shiang Liao、Wei-Ting Hung、Wen-Bin Yang、Jim-Min Fang

  DOI：10.1021/jo800234x

  日期：2008.5.1

  practical method has been developed for conversion of unprotected and unmodified aldoses to aldo-benzimidazoles and aldo-naphthimidazoles. Using iodine as an oxidant or promoter in acetic acid solution, a series of mono-, di-, and trialdoses, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with o-phenylenediamine or 2,3-naphthalenediamine at room

  已经开发了一种实用的方法，用于将未保护的和未修饰的醛糖转化为醛基-苯并咪唑和醛基-萘并咪唑。使用碘作为乙酸溶液中的氧化剂或助催化剂，在室温下，一系列单，双和三官能团（包括含有羧基和乙酰胺基的那些）与邻苯二胺或2,3-萘二胺发生氧化缩合反应以高收率得到醛-苯并咪唑和醛-萘并咪唑产物。在这种温和的反应条件下，没有发生糖苷键的切割。糖的组成分析通过荧光萘并咪唑衍生物的HPLC分析来实现。
• Studies on saccharide benzimidazoles: 2-(β-D-gulofuranosyl)benzimidazole and 2-(β-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency
  作者：Mohammed A.E. Sallam、Dalia M.S.A. Salem、Gorgina M.H. Labib、Trevena N.M.A. Youssef、Koichi Matsuo

  DOI：10.1016/j.carres.2020.108073

  日期：2020.10

  2-(D-gulo-) and 2-(D-gluco-)benzimidazole C-nucloside analogs have been prepared by condensation of o-phenylenediamine dihydrochloride derivatives with D-gulonic acid-γ-lactone and D-gluconic acid-γ-lactone, separately. Acid catalyzed dehydrative cyclization of the acyclic benzimidazole C-nucleoside afforded the corresponding 2-(β-D-gulo-) and 2-(β-D-gluco-)furanosyl benzimidazole C-nucleoside analogs. The

  通过邻苯二胺二盐酸盐衍生物与 D-古洛糖酸-γ-内酯和 D-葡萄糖酸缩合制备了一系列无环 2-(D-gulo-) 和 2-(D-gluco-) 苯并咪唑 C-核苷类似物酸-γ-内酯，分开。无环苯并咪唑C-核苷的酸催化脱水环化得到相应的2-(β-D-gulo-)和2-(β-D-葡糖-)呋喃糖基苯并咪唑C-核苷类似物。获得的C-核苷类似物的结构和异头构型通过高碘酸盐氧化、1H NMR、UV和圆二色性(CD)光谱确定。已使用抗菌生物膜试验研究了 C-核苷类似物的防污性能。2-(D-gulo-) 和 2-(D-gluco-) 苯并咪唑类似物可用于抑制海洋细菌的生长，并且不会对周围的海水造成任何不良影响。
• Yadav, Tej Bahadur; Singh, Virendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 12, p. 1536 - 1539
  作者：Yadav, Tej Bahadur、Singh, Virendra

  DOI：——

  日期：——