2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiourea | 2592-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiourea
• CAS: 2592-36-1
• 化学式: C₂₇H₃₈N₂O₁₇S
• 分子量: 694.668
• InChiKey: GIJCZAHXWCIAOQ-SVRUBWSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  261.66
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiourea 在 四丁基溴化铵 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 2-(5-hydroxyl-4H-pyran-4-one)-methyl-α-D-glucopyranosyl-(1→4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881
• 作为产物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 在 三乙基硅烷 、 碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.08h， 生成 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl isothiourea
  参考文献：
  名称：

  Efficient synthesis of thioglycosylated kojic acid bys-glycosyl isothiouronium salts

  摘要：

  In this study, 7-S-glycosides of kojic acid were designed and synthesized as mimics of its 7-O-glycosides to improve its water solubility and metabolic stability. To achieve this synthesis, a one-pot approach involving S-glycosyl isothiouronium salts generated in situ as key intermediates was developed by using 7-chloro-kojic acid as the alkylation reagent. A series of water soluble 7-S-glycosides of kojic acid, incorporating monosaccharides and disaccharides, were prepared using this protocol. Thus, this work offers a mild, convenient, and efficient approach for the synthesis of 7-S-glycosides of kojic acid in medium to good yields.[GRAPHICS].

  DOI：

  10.1080/07328303.2016.1261881

文献信息

• Reaction of 1,2-trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars
  作者：Farid M. Ibatullin、Konstantin A. Shabalin、Janne V. Jänis、Alexander G. Shavva

  DOI：10.1016/j.tetlet.2003.08.120

  日期：2003.10

  The reaction of 1,2-trans-glycosyl acetates with thiourea Under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and Subsequent alkylation or acylation of the in situ formed 1-thioaldose. (C) 2003 Elsevier Ltd. All rights reserved.