methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside | 1332641-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside
• CAS: 1332641-37-8
• 化学式: C₄₉H₅₃NO₉
• 分子量: 799.961
• InChiKey: FWZCXWDAFHPJGD-YZGLDEBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  106.1
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside 在 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.12h， 以40%的产率得到methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis

  摘要：

  Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for alpha-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(alpha 1 -> 3)Glc and Glc(alpha 1 -> 3) Man disaccharides representing the linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis. These (N1 -> 3)-linked pseudodisaccharides were found to have some alpha-Glucosidase II inhibitory activity, while two other (N1 -> 6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.046
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide 在 四丁基溴化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 56.0h， 生成 methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside 、 methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis

  摘要：

  Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for alpha-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(alpha 1 -> 3)Glc and Glc(alpha 1 -> 3) Man disaccharides representing the linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis. These (N1 -> 3)-linked pseudodisaccharides were found to have some alpha-Glucosidase II inhibitory activity, while two other (N1 -> 6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.046