naphthyl 2-O-crotonyl-3,4,6-tri-O-methyl-β-D-glucopyranoside | 194423-66-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: naphthyl 2-O-crotonyl-3,4,6-tri-O-methyl-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-4,5-dimethoxy-6-(methoxymethyl)-2-naphthalen-2-yloxyoxan-3-yl] (E)-but-2-enoate
• CAS: 194423-66-0
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: UGVQVQRBSBIOKB-OBLFYYNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙基溴化镁 、 naphthyl 2-O-crotonyl-3,4,6-tri-O-methyl-β-D-glucopyranoside 在 copper(I) bromide dimethylsulfide complex 作用下， 生成 naphthyl 2-O-(3-(S)-methylpentanoyl)-3,4,6-tri-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Naphthyl as a chiral auxiliary in an asymmetric 1,4-addition reaction

  摘要：

  Naphthyl 3,4,6-tri-O-methyl-beta-D-glucopyranoside, easily synthesized from tri-O-acetyl-D-glucal, has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6-tetra-O-methyl-beta-D-glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and pi-stacking effects, is proposed on the basis of the observed results. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00249-8
• 作为产物：
  描述：

  萘-2-酚钾 在 18-冠醚-6 、 3 A molecular sieve 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 63.0h， 生成 naphthyl 2-O-crotonyl-3,4,6-tri-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Naphthyl as a chiral auxiliary in an asymmetric 1,4-addition reaction

  摘要：

  Naphthyl 3,4,6-tri-O-methyl-beta-D-glucopyranoside, easily synthesized from tri-O-acetyl-D-glucal, has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6-tetra-O-methyl-beta-D-glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and pi-stacking effects, is proposed on the basis of the observed results. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00249-8