(R)-3-benzoyloxy-4-pentene-1-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside | 206348-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-benzoyloxy-4-pentene-1-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
• CAS: 206348-86-9
• 化学式: C₄₆H₄₀O₁₂
• 分子量: 784.816
• InChiKey: ACGVZUSCWJMBMB-BDAGRHJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  58.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (R)-3-benzoyloxy-4-pentene-1-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 168.0h， 以90%的产率得到(R)-3-hydroxy-4-pentene-1-yl α-D-mannopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives

  摘要：

  1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy-3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee=99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed into the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ols 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation of (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate afforded the corresponding mannopyranosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00052-4
• 作为产物：
  描述：

  5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-pent-1-en-3-ol 在 吡啶 、 Candida cylindracea lipase 、 sodium hydroxide 、 phosphate buffer 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 124.0h， 生成 (R)-3-benzoyloxy-4-pentene-1-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives

  摘要：

  1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy-3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee=99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed into the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ols 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation of (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate afforded the corresponding mannopyranosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00052-4