methyl 2-O-1-naphthyl acetyl-6-O-trityl-α-D-glucopyranoside | 813467-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2-O-1-naphthyl acetyl-6-O-trityl-α-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-methoxy-6-(trityloxymethyl)oxan-3-yl] 2-naphthalen-1-ylacetate
• CAS: 813467-60-6
• 化学式: C₃₈H₃₆O₇
• 分子量: 604.7
• InChiKey: VJQMAWXDPVTUII-VDLPFXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-1-naphthyl acetyl-6-O-trityl-α-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到methyl 2-O-1-naphthyl acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regioselective Acylation of Secondary Hydroxyl Groups by Means BOP‐Cl

  摘要：

  Methyl 2-O-acyl alpha-D-glucopyranosides are regioselectively formed with good yields by acylation of the correspondent 6-O-trityl pyranosides with carboxylic acids and (BOP-Cl). No acyl migration was observed in the deblocking of the primary hydroxyl group with p-toluensulfonic acid.

  DOI：

  10.1081/scc-200036630
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 4-二甲氨基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 反应 28.0h， 生成 methyl 2-O-1-naphthyl acetyl-6-O-trityl-α-D-glucopyranoside
  参考文献：
  名称：

  Regioselective Acylation of Secondary Hydroxyl Groups by Means BOP‐Cl

  摘要：

  Methyl 2-O-acyl alpha-D-glucopyranosides are regioselectively formed with good yields by acylation of the correspondent 6-O-trityl pyranosides with carboxylic acids and (BOP-Cl). No acyl migration was observed in the deblocking of the primary hydroxyl group with p-toluensulfonic acid.

  DOI：

  10.1081/scc-200036630

文献信息

• Regioselective Acylation of Secondary Hydroxyl Groups by Means BOP‐Cl
  作者：Renato Dalpozzo、Antonio De Nino、Loredana Maiuolo、Antonio Procopio、Giovanni Sindona、Antonio Tagarelli

  DOI：10.1081/scc-200036630

  日期：2004.12.31

  Methyl 2-O-acyl alpha-D-glucopyranosides are regioselectively formed with good yields by acylation of the correspondent 6-O-trityl pyranosides with carboxylic acids and (BOP-Cl). No acyl migration was observed in the deblocking of the primary hydroxyl group with p-toluensulfonic acid.