Chloro-acetic acid 1-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-allyl ester | 206348-78-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Chloro-acetic acid 1-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-allyl ester
• 英文别名: 5-[2,3-Dimethylbutan-2-yl(dimethyl)silyl]oxypent-1-en-3-yl 2-chloroacetate；5-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxypent-1-en-3-yl 2-chloroacetate
• CAS: 206348-78-9
• 化学式: C₁₅H₂₉ClO₃Si
• 分子量: 320.932
• InChiKey: YUUAUDLFXMANOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid 1-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-allyl ester 在 吡啶 、 sodium hydroxide 、 phosphate buffer 、 pseudomonas lipase 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 18.16h， 生成 (S)-3-benzoyloxy-4-pentene-1-ol
  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：

  pent-4-ene-1,3-diol 在 吡啶 、 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Chloro-acetic acid 1-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-allyl ester
  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

文献信息

• Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives
  作者：Frank Bien、Thomas Ziegler

  DOI：10.1016/s0957-4166(98)00052-4

  日期：1998.3

  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.