tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate | 1274953-83-1

• 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: tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate
• CAS: 1274953-83-1
• 化学式: C₁₈H₃₇NO₃Si
• 分子量: 343.582
• InChiKey: HWTVSOZBHDQXEI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate 在 potassium dihydrogenphosphate 、 Hoveyda-Grubbs catalyst second generation 、 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 tert-butyl {(4R,6E,8S,10E,12S,14S,16S)-4,14,16-tris{[tert-butyl(dimethyl)silyl]oxy}-8,12-dihydroxy-18-[(4-methoxybenzyl)-oxy]octadeca-6,10-dien-1-yl}carbamate
  参考文献：
  名称：

  Enantio- and Diastereoselective Synthesis of (E)-1,5-syn-Diols: Application to the Synthesis of the C(23)−C(40) Fragment of Tetrafibricin

  摘要：

  A highly stereoselective synthesis of (E)-1,5-syn-diols 6 Is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 In 72-98% yields with > 95% ee and > 20:1 dr. Application of this method to the synthesis of the tetraflbricin C(23)-C(40) fragment 19 is described.

  DOI：

  10.1021/ol2003836
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 三丁基膦 、 (-)-B-methoxydiisopinocampheylborane 作用下， 以 乙醚 、 水 为溶剂， 反应 7.5h， 生成 tert-butyl ((4R)-4-{[tert-butyl(dimethyl)silyl]oxy}hept-6-en-1-yl)carbamate
  参考文献：
  名称：

  Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: application to the synthesis of the C(23)–C(40) fragment of tetrafibricin

  摘要：

  Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.008