N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide | 172950-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS: 172950-34-4
• 化学式: C₂₉H₃₈N₄O₁₀
• 分子量: 602.642
• InChiKey: QWEBLYSXXXIYMF-IGVIKAMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  193.93
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 在 palladium on activated charcoal 氢气 作用下， 反应 5.0h， 以79%的产率得到
  参考文献：
  名称：

  Methyl 3-amino-3-deoxy-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside: An inhibitor of UDP-d-galactose: β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucose(1 → 3)-α-d-galactopyranosyltransferase

  摘要：

  UDP-D-galactose: beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-D-glucose alpha(1 --> 3)-D-galactopyranosyltransferase [E.C. 2.4.1.151] transfers D-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with K-i = 104 mu M. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.

  DOI：

  10.1016/0008-6215(95)00165-p
• 作为产物：
  描述：

  甲基 3,6-二-O-苄基-2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)吡喃己糖苷 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 乙二胺 、 正丁醇 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Methyl 3-amino-3-deoxy-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside: An inhibitor of UDP-d-galactose: β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucose(1 → 3)-α-d-galactopyranosyltransferase

  摘要：

  UDP-D-galactose: beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-D-glucose alpha(1 --> 3)-D-galactopyranosyltransferase [E.C. 2.4.1.151] transfers D-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with K-i = 104 mu M. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.

  DOI：

  10.1016/0008-6215(95)00165-p