(R)-1-dimethylthexylsilyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside | 206257-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-dimethylthexylsilyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
• CAS: 206257-81-0
• 化学式: C₄₆H₅₂O₁₁Si
• 分子量: 808.998
• InChiKey: XWELVTSJJDJFBV-FOBFHTMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  58.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (R)-1-dimethylthexylsilyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以82%的产率得到(R)-1-hydroxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2
• 作为产物：
  描述：

  Chloro-acetic acid 1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-allyl ester 在 sodium hydroxide 、 phosphate buffer 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Pseudomonas Amano PS lipase 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-1-dimethylthexylsilyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2