[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(E)-3-methoxy-3-oxoprop-1-enyl]sulfanyloxan-2-yl]methyl benzoate | 1423128-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(E)-3-methoxy-3-oxoprop-1-enyl]sulfanyloxan-2-yl]methyl benzoate
• CAS: 1423128-35-1
• 化学式: C₃₈H₃₂O₁₁S
• 分子量: 696.731
• InChiKey: UDZYPZOGZAHOPY-CUTSKSCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 在 二硫化碳 、 sodiumsulfide nonahydrate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(E)-3-methoxy-3-oxoprop-1-enyl]sulfanyloxan-2-yl]methyl benzoate
  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

文献信息

• Stereoselective Synthesis of β-Glycosyl Thiols and Their Synthetic Applications
  作者：Manas Jana、Anup Kumar Misra

  DOI：10.1021/jo302115k

  日期：2013.3.15

  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.