rel-(2R,3R,4R)-trans-5-(p-methoxyphenyl)-3-(methoxymethoxy)-4-methyl-1-hex-5-en-1-ol | 143191-38-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rel-(2R,3R,4R)-trans-5-(p-methoxyphenyl)-3-(methoxymethoxy)-4-methyl-1-hex-5-en-1-ol
• 英文别名: (E,2S,3S,4S)-3-(methoxymethoxy)-6-(4-methoxyphenyl)-4-methylhex-5-en-2-ol
• CAS: 143191-38-2
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: LQPXAGRRIRXWED-JETXNHJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rel-(2R,3R,4R)-trans-5-(p-methoxyphenyl)-3-(methoxymethoxy)-4-methyl-1-hex-5-en-1-ol 在 四氧化锇 吡啶 、 双氧水 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 57.0h， 生成 rel-(2S,3S,4S,5S,6R)-tetrahydro-5-(methoxymethoxy)-2-(p-methoxyphenyl)-4,6-dimethyl-2H-pyran-3,4-diol
  参考文献：
  名称：

  C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols

  摘要：

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

  DOI：

  10.1021/jo00047a020
• 作为产物：
  描述：

  cis,cis-2-methyl-3-hydroxy-4-(iodomethyl)-γ-butyrolactone 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 92.17h， 生成 rel-(2R,3R,4R)-trans-5-(p-methoxyphenyl)-3-(methoxymethoxy)-4-methyl-1-hex-5-en-1-ol
  参考文献：
  名称：

  C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols

  摘要：

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

  DOI：

  10.1021/jo00047a020

文献信息

• C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols
  作者：David J. Hart、Vincent Leroy、Gregory H. Merriman、David G. J. Young

  DOI：10.1021/jo00047a020

  日期：1992.10

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.