methyl 6-deoxy-6-[N'-cyclohexanyl-N''-(benzothiazol-2-yl)]guanidino-α-D-glucopyranoside | 1021460-94-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-[N'-cyclohexanyl-N''-(benzothiazol-2-yl)]guanidino-α-D-glucopyranoside
• CAS: 1021460-94-5
• 化学式: C₂₁H₃₀N₄O₅S
• 分子量: 450.559
• InChiKey: ZZBPMCWKUWLFQA-FTWQHDNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  128.46
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-deoxy-6-[N'-cyclohexanyl-N''-(benzothiazol-2-yl)]guanidino-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到methyl 6-deoxy-6-[N'-cyclohexanyl-N''-(benzothiazol-2-yl)]guanidino-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and bioactivity of novel methyl 6-deoxy-6-(N′-alkyl/aryl-N″-benzothiazol-2-yl)guanidino-α-d-glucopyranosides

  摘要：

  A series of new methyl 6-deoxy-6-[N'-alkyl/aryl-N"-(benzothiazol-2-yl)]guanidino-alpha-D-glucopyranosides were obtained from the reaction of an alkyl/aryl amine in the presence of HgCl2 and sugar-thiourea derivatives, followed by the removal of protecting groups. The sugar-thiourea derivatives were obtained from the treatment of 2-aminobenzothiazole derivatives with methyl 2,3,4-tri-O-acetyl-6-deoxy-6-isothiocyanato-alpha-D-glucopyranoside in dry pyridine. Some of the synthesized guanidines displayed anti-influenza activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.001

文献信息

• An expedient one-step synthesis of polysubstituted guanidinoglucosides using HgO–4 Å molecular sieves as catalyst
  作者：Yong-Hua Liu、Ling-Hua Cao

  DOI：10.1016/j.carres.2008.07.016

  日期：2008.9

  A novel one-step method of preparing polysubstituted guanidinoglucosides using peracetylated methyl 6-deoxy-6-thioureidoglucosides as starting materials and employing HgO in combination with molecular sieves as an efficient catalyst is reported. The structures of three methyl 2,3,4-tri-O-acetyl-6-[N(2)-(benzothiazol-2-yl)-N(3)-(oxydi-1,2-ethandiyl)]guanidi no-6-deoxy-alpha-d-glucopyranosides were unambiguously

  报道了一种新的一步法制备多取代的胍基葡糖苷的方法，该方法以过乙酰化的甲基6-脱氧-6-硫脲基葡糖苷为原料，并与分子筛结合使用HgO作为有效催化剂。三个甲基2,3,4-三-O-乙酰基-6- [N（2）-（苯并噻唑-2-基）-N（3）-（氧基二1,2-ethandiyl）]的结构通过X射线晶体学明确地确认了-6-脱氧-α-d-吡喃葡萄糖苷。该方法提供了高收率的新化合物，也为合成氨基甲酸酯保护的胍提供了有希望的途径。