methyl 4-O-(5-azido-9-α-D-glucopyranosyloxy-7-thianonyl)-α-D-glucopyranoside | 172949-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(5-azido-9-α-D-glucopyranosyloxy-7-thianonyl)-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[2-[2-azido-6-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxyhexyl]sulfanylethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 172949-89-2
• 化学式: C₂₁H₃₉N₃O₁₂S
• 分子量: 557.62
• InChiKey: GXCBDUVQIFOHJB-MGEHWHOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  227
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(5-azido-9-α-D-glucopyranosyloxy-7-thianonyl)-α-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 反应 1.0h， 以99%的产率得到methyl 4-O-(5-amino-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-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 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

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.