(2R,6R,10R,13RS)-13-benzyloxy-1,16-bis-(tert-butyldimethylsilyloxy)-2,6,10-trimethylhexadecan-6-ol | 1358982-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,6R,10R,13RS)-13-benzyloxy-1,16-bis-(tert-butyldimethylsilyloxy)-2,6,10-trimethylhexadecan-6-ol
• CAS: 1358982-79-2
• 化学式: C₃₈H₇₄O₄Si₂
• 分子量: 651.174
• InChiKey: GGLHJGMIJFCMKV-OQKCAAMASA-N

反应信息

• 作为反应物：
  描述：

  (2R,6R,10R,13RS)-13-benzyloxy-1,16-bis-(tert-butyldimethylsilyloxy)-2,6,10-trimethylhexadecan-6-ol 在 氨 、 lithium 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到(4RS,7R,11R,12R,15R)-1,16-bis-(tert-butyldimethylsilyloxy)-7,11,15-trimethylhexadecane-4,11-diol
  参考文献：
  名称：

  Structure–activity relationship of α hormones, the mating factors of phytopathogen Phytophthora

  摘要：

  The mating hormones alpha 1 and alpha 2 induce sexual reproduction of the phytopathogenic genus Phytophthora. To demonstrate the structural elements responsible to hormonal activity, 17 derivatives of alpha 1 and alpha 2 were synthesized and their hormonal activity (oospore-inducing activity) was evaluated. The terminal ester derivatives of alpha 1 (diacetate and dibenzoate) retained the hormonal activity, whereas a dicarbamate derivative completely suppressed the activity. Even monocarbamates showed weak activities; among them the 1-O-carbamate was less active than 16-O-carbamate, suggesting that the 1-OH group is a little more important than 16-OH. Dihydro, dehydro, and demethyl derivatives exhibited the minimum level of activity. Surviving activity of 15-epi-alpha 1 suggested a less importance of this stereochemistry. Contrary to alpha 1, not only the terminal diacetate derivative but also monoacetates of alpha 2 exhibited no or little activity. Among the monoacetates, 1-O-acetyl-alpha 2 exhibited little yet relatively better activity than the others. No activity was observed for mono- and dicarbamoyl derivatives of alpha 2. Dihydro alpha 2 with the saturated double bond lost most of the activity. These findings suggest that both the mating hormones alpha 1 and alpha 2 require most of the functional (hydroxyl, keto, and olefinic) groups they possess in their natural form for inducing the sexual reproduction of Phytophthora. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.015
• 作为产物：
  描述：

  (4RS,7R,15R)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-7,11,15-trimethyl-4-hexadecyl benzyl ether 在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 13.0h， 以58%的产率得到(2R,6R,10R,13RS)-13-benzyloxy-1,16-bis-(tert-butyldimethylsilyloxy)-2,6,10-trimethylhexadecan-6-ol
  参考文献：
  名称：

  Structure–activity relationship of α hormones, the mating factors of phytopathogen Phytophthora

  摘要：

  The mating hormones alpha 1 and alpha 2 induce sexual reproduction of the phytopathogenic genus Phytophthora. To demonstrate the structural elements responsible to hormonal activity, 17 derivatives of alpha 1 and alpha 2 were synthesized and their hormonal activity (oospore-inducing activity) was evaluated. The terminal ester derivatives of alpha 1 (diacetate and dibenzoate) retained the hormonal activity, whereas a dicarbamate derivative completely suppressed the activity. Even monocarbamates showed weak activities; among them the 1-O-carbamate was less active than 16-O-carbamate, suggesting that the 1-OH group is a little more important than 16-OH. Dihydro, dehydro, and demethyl derivatives exhibited the minimum level of activity. Surviving activity of 15-epi-alpha 1 suggested a less importance of this stereochemistry. Contrary to alpha 1, not only the terminal diacetate derivative but also monoacetates of alpha 2 exhibited no or little activity. Among the monoacetates, 1-O-acetyl-alpha 2 exhibited little yet relatively better activity than the others. No activity was observed for mono- and dicarbamoyl derivatives of alpha 2. Dihydro alpha 2 with the saturated double bond lost most of the activity. These findings suggest that both the mating hormones alpha 1 and alpha 2 require most of the functional (hydroxyl, keto, and olefinic) groups they possess in their natural form for inducing the sexual reproduction of Phytophthora. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.015