(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)hex-5-ene-1,3-diol | 140479-50-1

• 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: (2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)hex-5-ene-1,3-diol
• 英文别名: (2R,3R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}hex-5-ene-1,3-diol；(2R,3R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]hex-5-ene-1,3-diol
• CAS: 140479-50-1
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: AUZZEYUGQGIJAU-DENIHFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)hex-5-ene-1,3-diol 在 四丁基氟化铵 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.17h， 生成 (4R,5S)-trans-4-allyl-5-(((benzyloxy)methoxy)methyl)-2,2-dimethyl-1,3-dioxane
  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：

  Acetic acid (E)-(R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-hex-3-enyl ester 在 氢氧化钾 、 二甲基硫 、 pH 7 buffer 、 臭氧 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)hex-5-ene-1,3-diol
  参考文献：
  名称：

  Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (hydroxymethyl)acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.

  DOI：

  10.1016/0040-4039(91)80449-g

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.
• Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl)acetaldehydes (BHYMA*)
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/0040-4039(91)80449-g

  日期：1991.11

  MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (hydroxymethyl)acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.