(2S,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-ol | 152669-27-7

• 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,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-ol
• 英文别名: (2S,3S,4R)-1-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxymethoxymethyl]-4-methylhex-5-en-3-ol
• CAS: 152669-27-7
• 化学式: C₃₃H₄₄O₅Si
• 分子量: 548.795
• InChiKey: LCAFEAQORFOMEA-LNGZGTQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-ol 在 jones reagent 作用下， 以80%的产率得到(2S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-one
  参考文献：
  名称：

  Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  The asymmetric synthesis of epimeric alpha-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotyltributyltin to asymmetrized bis(hydroxymethyl)acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both enantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.

  DOI：

  10.1016/s0040-4039(00)73941-4
• 作为产物：
  描述：

  (S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propan-1-ol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-ol
  参考文献：
  名称：

  Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  The asymmetric synthesis of epimeric alpha-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotyltributyltin to asymmetrized bis(hydroxymethyl)acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both enantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.

  DOI：

  10.1016/s0040-4039(00)73941-4

文献信息

• Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)
  作者：Giuseppe Guanti、Luca Banfi、M.Teresa Zannetti

  DOI：10.1016/s0040-4039(00)73941-4

  日期：1993.1

  The asymmetric synthesis of epimeric alpha-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotyltributyltin to asymmetrized bis(hydroxymethyl)acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both enantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.