methyl 2,3,6-tri-O-benzyl-4-O-(5,6-isopropylidenedioxyhexyl)-α-D-glucopyranoside | 172949-79-0

• 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-benzyl-4-O-(5,6-isopropylidenedioxyhexyl)-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-5-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)butoxy]-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 172949-79-0
• 化学式: C₃₇H₄₈O₈
• 分子量: 620.783
• InChiKey: KPXQTWSKXALOHI-FJUAQIJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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 、 sodium methylate 、 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 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：

  1,2-O-isopropylidenehexane-1,2,6-triol 6-p-toluenesulfonate 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(5,6-isopropylidenedioxyhexyl)-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

文献信息

• Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme
  作者：Jochen Lehmann、Markus Schmidt-Schuchardt

  DOI：10.1016/0008-6215(95)00089-c

  日期：1995.10

  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.