(2S,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-ol | 146512-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-ol
• 英文别名: (2S,3S)-1-((tert-butyldiphenylsilyl)oxy)-2-((((p-methoxybenzyl)oxy)methoxy)methyl)hex-5-en-3-ol；(2S,3S)-1-[(tert-butyldiphenylsilyl)oxy]-2-({[(p-methoxybenzyl)oxy]methoxy}methyl)hex-5-en-3-ol；(2S,3S)-1-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxymethoxymethyl]hex-5-en-3-ol
• CAS: 146512-59-6
• 化学式: C₃₂H₄₂O₅Si
• 分子量: 534.768
• InChiKey: BHWSKDHTJTUTCS-DHIFEGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 、 4 A molecular sieve 、 四丁基氟化铵 、 对甲苯磺酸 、 臭氧 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 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)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal 在 4 Angstroem MS 、 二异丁基氢化铝 、 magnesium bromide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.17h， 生成 (2S,3S)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-ol
  参考文献：
  名称：

  使用DIBALH / MgBr 2系统，由保护基控制的非对映选择性还原衍生自THYM *的双保护α，α-双（羟甲基）酮

  摘要：

  新型手性结构单元THYM * 1和BHYMA * 2衍生的双保护α，α-双（羟甲基）酮5的还原反应具有良好的立体选择性（从85:15至97：3）。通过采用DIBALH和MgBr的组合两个保护基团和适当的选择2 ·的Et 2 O.

  DOI：

  10.1016/s0040-4039(00)73940-2

文献信息

• Highly Versatile Stereoselective Synthesis of All Eight Stereoisomers of Branched-Chain Triols Starting from Asymmetrized Bis(hydroxymethyl)acetaldehydes (BHYMA)
  作者：Luca Banfi、Giuseppe Guanti、Maria Teresa Zannetti

  DOI：10.1021/jo00129a029

  日期：1995.12

  All possible stereoisomers of triols of general formula 5 (R(1) allyl, R(2) = Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHY-MA*), a novel chiral building block prepared through a chemoenzymatic methodology. This goal was realized through a sequence of protecting group-controlled nucleophilic additions and/or reductions performed on two side arms of this versatile building block.
• 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 reduction of diprotected α,α-bis(hydroxymethyl)ketones derived from THYM*, using the DIBALH / MgBr2 system
  作者：Giuseppe Guanti、Luca Banfi、Renata Riva、M.Teresa Zannetti

  DOI：10.1016/s0040-4039(00)73940-2

  日期：1993.1

  The reduction of diprotected α,α-bis(hydroxymethyl)ketones 5, derived from the novel chiral building blocks THYM* 1 and BHYMA* 2 has been realized with good to excellent stereoselectivity (from 85:15 to 97:3), through a appropriate choice of the two protecting groups and by employing the combination of DIBALH and MgBr2·Et2O.

  新型手性结构单元THYM * 1和BHYMA * 2衍生的双保护α，α-双（羟甲基）酮5的还原反应具有良好的立体选择性（从85:15至97：3）。通过采用DIBALH和MgBr的组合两个保护基团和适当的选择2 ·的Et 2 O.