2-p-tolylysulfonylethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 172949-87-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-p-tolylysulfonylethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• CAS: 172949-87-0
• 化学式: C₂₃H₃₀O₁₃S
• 分子量: 546.549
• InChiKey: ZDAGAJVZPVFZLB-ZQGJOIPISA-N

物化性质

• 沸点：
  617.8±55.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  167.03
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-p-tolylysulfonylethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 methyl 4-O-(5-azido-9-α-D-glucopyranosyloxy-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：

  allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 2-p-tolylysulfonylethyl 2,3,4,6-tetra-O-acetyl-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