methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside | 172949-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside
• CAS: 172949-86-9
• 化学式: C₂₆H₃₇N₃O₁₂S
• 分子量: 615.659
• InChiKey: BFBPHPFOJHWRAY-YQPSVUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  198.72
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 methyl 4-O-(5-azido-9-α-maltosyloxy-7-thianonyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme

  摘要：

  By coupling methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolysulfonyloxyhexyl)-alpha-D-glucopyranoside with 2-benzoylthioethyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside, a spacer-modified disaccharide derivative, methyl 4-O-(5-azido-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, was obtained and then enzymatically glucosylated to yield the spacer-modified tri- and tetra-saccharide methyl 4-O-(5-azido-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-azido-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, respectively, the extended spacer spanning the length of two (1 --> 4)-linked pyranosyl units. The corresponding amines methyl 4-O-(5-amino-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-amino-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, obtained by catalytic reduction, carry the basic functionality in a spacer position to allow ionic interaction with a catalytically active acidic group in porcine pancreatic alpha-amylase (PPA). Optimal inhibition of enzymic activity is by methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside where three of the five subsites are occupied by glucosyl units and the spacer spanning the remaining subsites positions the amino group near the catalytic site.

  DOI：

  10.1016/0008-6215(95)00089-c
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(5,6-isopropylidenedioxyhexyl)-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 三氟乙酸 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.83h， 生成 methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme

  摘要：

  By coupling methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolysulfonyloxyhexyl)-alpha-D-glucopyranoside with 2-benzoylthioethyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside, a spacer-modified disaccharide derivative, methyl 4-O-(5-azido-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, was obtained and then enzymatically glucosylated to yield the spacer-modified tri- and tetra-saccharide methyl 4-O-(5-azido-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-azido-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, respectively, the extended spacer spanning the length of two (1 --> 4)-linked pyranosyl units. The corresponding amines methyl 4-O-(5-amino-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-amino-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, obtained by catalytic reduction, carry the basic functionality in a spacer position to allow ionic interaction with a catalytically active acidic group in porcine pancreatic alpha-amylase (PPA). Optimal inhibition of enzymic activity is by methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside where three of the five subsites are occupied by glucosyl units and the spacer spanning the remaining subsites positions the amino group near the catalytic site.

  DOI：

  10.1016/0008-6215(95)00089-c