(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene | 175613-21-5

• 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: (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene
• 英文别名: [(2R,3S,4R)-2-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-3-[(4-methoxyphenyl)methoxy]-4-methyloct-7-enyl] methanesulfonate
• CAS: 175613-21-5
• 化学式: C₂₇H₄₈O₆SSi
• 分子量: 528.826
• InChiKey: BVVDPPNVSHDNRB-NOOIUNMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以88%的产率得到(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-5-<(4-methoxybenzyl)oxy>-4,6-dimethyl-9-decene
  参考文献：
  名称：

  Synthesis of the C1−C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin

  摘要：

  Compound 40 containing the C-1-C-21 region of tautomycin has been synthesized. The two halves (4 and 5) of this spirocyclic section were each constructed using Matteson's chloromethylene insertion reaction. Cr/Ni-mediated coupling of compounds 4 and 5 resulted in a structure containing the C-1-C-21 section of tautomycin. Oxidation of the resultant allylic alcohol to the ketone and removal of the alpha,beta unsaturation yielded compound 39. Treatment with DDQ removed both PMB protecting groups and allowed the spirocyclic ketal to form producing compound 40, ready for further extension to the natural product tautomycin.

  DOI：

  10.1021/jo952083l
• 作为产物：
  描述：

  (1S,2S,6R,8S)-4-[(2S,3S,4R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-(4-methoxy-benzyloxy)-4-methyl-oct-7-enyl]-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 在 sodium hydroxide 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene
  参考文献：
  名称：

  Synthesis of the C1−C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin

  摘要：

  Compound 40 containing the C-1-C-21 region of tautomycin has been synthesized. The two halves (4 and 5) of this spirocyclic section were each constructed using Matteson's chloromethylene insertion reaction. Cr/Ni-mediated coupling of compounds 4 and 5 resulted in a structure containing the C-1-C-21 section of tautomycin. Oxidation of the resultant allylic alcohol to the ketone and removal of the alpha,beta unsaturation yielded compound 39. Treatment with DDQ removed both PMB protecting groups and allowed the spirocyclic ketal to form producing compound 40, ready for further extension to the natural product tautomycin.

  DOI：

  10.1021/jo952083l