(Methoxycarbonyl)octyl 2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside | 77111-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Methoxycarbonyl)octyl 2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxynonanoate
• CAS: 77111-92-3
• 化学式: C₂₄H₃₉NO₁₁
• 分子量: 517.574
• InChiKey: YTCCSAVTIRXVNI-JTYPQFNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (Methoxycarbonyl)octyl 2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 Lindlar's catalyst 吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 乙二醇甲醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 222.5h， 生成 (Methoxycarbonyl)octyl 2-acetamido-3-deoxy-3-amino-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007
• 作为产物：
  描述：

  D-GlcNAc 在 calcium sulfate 、 氰化汞 作用下， 以 苯 为溶剂， 反应 84.0h， 生成 (Methoxycarbonyl)octyl 2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007

文献信息

• Synthesis of 8-(methoxycarbonyl)octyl glycosides of O-α-l-rhamno-pyranosyl-(1 → 3)-O-α-l-rhamnopyranosyl-(1 →3)-2-acetamido-2,6-dideoxy-d-glucopyranose; models for the antigen of Pseudomonas aeruginosa Fisher immunotype 5
  作者：Derek Horton、Soth Samreth

  DOI：10.1016/s0008-6215(82)80027-x

  日期：1982.5
• Stannous triflate mediated glycosidations. A stereoselective synthesis of 2-amino 2-deoxy-β-D-glucopyranosides directly with the natural N-acetyl protecting group.
  作者：André Lubineau、Joëlle Le Gallic、Annie Malleron

  DOI：10.1016/s0040-4039(00)96690-5

  日期：1987.1
• LUBINEAU, ANDRE;LE, GALLIC JOELLE;MALLERON, ANNIE, TETRAHEDRON LETT., 28,(1987) N 42, 5041-5044
  作者：LUBINEAU, ANDRE、LE, GALLIC JOELLE、MALLERON, ANNIE

  DOI：——

  日期：——