(2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 | 358738-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯
• 英文名称: C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)thioformamide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-carbamothioyloxan-2-yl]methyl benzoate
• CAS: 358738-50-8
• 化学式: C₃₅H₂₉NO₉S
• 分子量: 639.683
• InChiKey: GIQMMENYWUCMEQ-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 potassium bromate 、 sodium dithionite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以86%的产率得到3,5-bis(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-thiadiazole
  参考文献：
  名称：

  Preparation of 3,5-bis-(β- d -glycopyranosyl)-1,2,4-thiadiazoles from C -(β- d -glycopyranosyl)thioformamides

  摘要：

  Acylated C-glycopyranosyl thioformamides of D-gluco, D-galacto, and D-xylo configuration were obtained by treating the corresponding glycosyl cyanides with hydrogen sulfide in the presence of triethylamine. The thioformamides gave 3,5-bis-(beta -D-glycopyranosyl)-1,2,4-thiadiazoles in reactions with potassium bromate and sodium dithionite in dichloromethane-water biphasic solvent mixture. Deprotected derivatives were prepared by Zemplen deacylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00444-6
• 作为产物：
  描述：

  (2R,3R,4R,5S,6S)-2-[(苯甲酰氧基)甲基]-6-氰基四氢-2H-吡喃-3,4,5-三基三苯甲酸酯 在 硫化氢 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以74%的产率得到(2R,3R,4S,5R,6R)-2-[(苯甲酰氧基)甲基]-6-硫代氨基甲酰四氢-2H-吡喃-3,4,5-三基三苯甲酸酯
  参考文献：
  名称：

  Preparation of 3,5-bis-(β- d -glycopyranosyl)-1,2,4-thiadiazoles from C -(β- d -glycopyranosyl)thioformamides

  摘要：

  Acylated C-glycopyranosyl thioformamides of D-gluco, D-galacto, and D-xylo configuration were obtained by treating the corresponding glycosyl cyanides with hydrogen sulfide in the presence of triethylamine. The thioformamides gave 3,5-bis-(beta -D-glycopyranosyl)-1,2,4-thiadiazoles in reactions with potassium bromate and sodium dithionite in dichloromethane-water biphasic solvent mixture. Deprotected derivatives were prepared by Zemplen deacylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00444-6

文献信息

• C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-d-glucopyranosyl-1,5-disubstituted and 5-β-d-glucopyranosyl-1,3-disubstituted variants
  作者：Katalin E. Szabó、András Páhi、László Somsák

  DOI：10.1016/j.tet.2017.05.014

  日期：2017.7

  Highly variable synthetic routes were elaborated toward trisubstituted C-glycopyranosyl 1,2,4-triazoles. N-Acyl-thioamide derivatives were obtained by acylation of O-perbenzoylated 2,6-anhydro-d-glycero-d-gulo-heptonothioamide by acid chlorides and of thioamides by O-perbenzoylated 2,6-anhydro-d-glycero-d-gulo-heptonoyl chloride. These precursors reacted with substituted hydrazines in a regioselective

  精心设计了高度可变的合成路线，以形成三取代的C-甘露糖基1,2,4-三唑。Ñ酰基硫代酰胺衍生物通过酰化得到ö -perbenzoylated 2,6-脱水- d -甘油基- d -庚糖酸氯化物和硫代酰胺通过-heptonothioamide ö -perbenzoylated 2,6-脱水- d -甘油基- d -庚-heptonoyl酰氯。这些前体以区域选择性的方式与取代的肼反应，生成3-β- d-吡喃葡萄糖基-1,5-二取代-和5-β- d-吡喃葡萄糖基-1,3-二取代-1,2,4-三唑。类似的N-酰基-2，6-脱水庚酰胺不能使上述三唑与肼结合。通过Zemplén方法对C-葡萄糖基1,2,4-三唑进行O-脱保护，得到的测试化合物没有抑制兔肌肉糖原磷酸化酶b的作用。
• Synthesis of substituted 2-(β-d-glucopyranosyl)-benzimidazoles and their evaluation as inhibitors of glycogen phosphorylase
  作者：Éva Bokor、Enikő Szilágyi、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2013.01.011

  日期：2013.11

  Microwave assisted condensation of O-perbenzoylated C-(beta-D-glucopyranosyl) formic acid with 1,2-diaminobenzenes in the presence of triphenylphosphite gave the corresponding O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in moderate yields. O-Perbenzoylated C-(beta-D-glucopyranosyl) formamide and -thioformamide were transformed into the corresponding ethyl C-(beta-D-glucopyranosyl) formimidate and -thioformimidate, respectively, by Et3O center dot BF4. Treatment of the formimidate with 1,2-diaminobenzenes afforded O-protected 2-(beta-D-glucopyranosyl)-benzimidazoles in good to excellent yields. Similar reaction of the thioformimidate gave these compounds in lower yields. The O-benzoyl protecting groups were removed by the Zemplen protocol. These test compounds were assayed against rabbit muscle glycogen phosphorylase (GP) b, the prototype of liver GP, the rate limiting enzyme of glycogen degradation. The best inhibitors were 2-(beta-D-glucopyranosyl)-4-methyl-benzimidazole (K-i = 2.8 mu M) and 2-(beta-D-glucopyranosyl)- naphtho[2,3-d] imidazole (K-i = 2.1 mu M) exhibiting a similar to 3-4 times stronger binding than the unsubstituted parent compound. (C) 2013 Elsevier Ltd. All rights reserved.
• 4(5)-Aryl-2-<i>C</i>-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase
  作者：Éva Bokor、Sándor Kun、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1021/acsmedchemlett.5b00361

  日期：2015.12.10

  Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(beta-D-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds were synthesized, and the latter showed the strongest inhibition against rabbit muscle glycogen phosphorylase b. Most efficient was 2-(beta-D-glucopyranosyl)-4(5)-(2-naphthyl)-imidazole (11b, K-i = 31 nM) representing the best nanomolar glucose derived inhibitor of the enzyme.