(3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-4-hydroxymethyl-pentanal | 1025875-63-1

• 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: (3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-4-hydroxymethyl-pentanal
• 英文别名: (3S,4S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,5-dihydroxypentanal
• CAS: 1025875-63-1
• 化学式: C₂₂H₃₀O₄Si
• 分子量: 386.563
• InChiKey: SFEIJVFVIKEUEY-RXVVDRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-4-hydroxymethyl-pentanal 在 4 A molecular sieve 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2-ethoxy-5-(hydroxymethyl)tetrahydropyran-4-ol
  参考文献：
  名称：

  Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane

  摘要：

  Asymmetrized tria(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported. Preparation of bottom half fragment 3 was achieved through a ''protecting group-controlled'' stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.

  DOI：

  10.1021/jo00058a036
• 作为产物：
  描述：

  (2S,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-ol 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 二甲基硫 、 臭氧 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (3S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-4-hydroxymethyl-pentanal
  参考文献：
  名称：

  Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane

  摘要：

  Asymmetrized tria(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported. Preparation of bottom half fragment 3 was achieved through a ''protecting group-controlled'' stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.

  DOI：

  10.1021/jo00058a036

文献信息

• Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano、M. Teresa Zannetti

  DOI：10.1021/jo00058a036

  日期：1993.3

  Asymmetrized tria(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported. Preparation of bottom half fragment 3 was achieved through a ''protecting group-controlled'' stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.