(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→1)-2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltopyranoside | 1423128-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→1)-2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1423128-73-7
• 化学式: C₄₀H₅₄O₂₆S
• 分子量: 982.919
• InChiKey: YDUOFCYYWDCIPC-ADJNRHBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  352
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranose 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 以84%的产率得到(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1→1)-2,3,6,2',3',4',6'-hepta-O-acetyl-1-thio-β-D-maltopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Glycosyl Thiols and Their Synthetic Applications

  摘要：

  A significantly fast reaction condition for the exclusive preparation beta-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.

  DOI：

  10.1021/jo302115k