3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-4-O-methyl-2-phthalimido-β-D-glucopyranose | 732247-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-4-O-methyl-2-phthalimido-β-D-glucopyranose
• CAS: 732247-03-9
• 化学式: C₃₅H₄₃NO₇Si
• 分子量: 617.814
• InChiKey: MRQTZULFPKAJKE-ITRDTHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-4-O-methyl-2-phthalimido-β-D-glucopyranose 在 四丁基氟化铵 、 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-methyl-D-glucopyranose
  参考文献：
  名称：

  Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis

  摘要：

  Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1 --> 4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.014
• 作为产物：
  描述：

  (tert-butyl)dimethylsilyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.0h， 生成 3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-4-O-methyl-2-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis

  摘要：

  Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1 --> 4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.014