naphthyl 2-O-(3-(S)-methylpentanoyl)-3,4,6-tri-O-methyl-β-D-glucopyranoside | 194423-67-1

• 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-(3-(S)-methylpentanoyl)-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] (3S)-3-methylpentanoate
• CAS: 194423-67-1
• 化学式: C₂₅H₃₄O₇
• 分子量: 446.541
• InChiKey: AWFVVUCCTCRSSA-VBTHIAJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  naphthyl 2-O-(3-(S)-methylpentanoyl)-3,4,6-tri-O-methyl-β-D-glucopyranoside 在 氢氧化钾 、 18-冠醚-6 作用下， 反应 4.0h， 以100%的产率得到(S)-3-甲基戊酸
  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 copper(I) bromide dimethylsulfide complex 、 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 65.0h， 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

文献信息

• Naphthyl as a chiral auxiliary in an asymmetric 1,4-addition reaction
  作者：Cinzia Chiappe、Giacomo Lo Moro、Paola Munforte

  DOI：10.1016/s0957-4166(97)00249-8

  日期：1997.7

  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.