methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside | 1582775-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside
• CAS: 1582775-54-9
• 化学式: C₂₇H₃₃N₃O₁₁
• 分子量: 575.573
• InChiKey: JNHAOEGACNCBOO-HBCWCQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  202.13
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

  摘要：

  The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.

  DOI：

  10.1021/ol500738g
• 作为产物：
  描述：

  p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 吡啶 、 咪唑 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 氢氟酸 、 双氧水 、 sodium methylate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides

  摘要：

  The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.

  DOI：

  10.1021/ol500738g