(2S,3R,9S,13S,14S)-14-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-1-phenyl-hexadec-15-ene-1,5,11-trione | 585535-28-0

• 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: (2S,3R,9S,13S,14S)-14-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-1-phenyl-hexadec-15-ene-1,5,11-trione
• CAS: 585535-28-0
• 化学式: C₅₆H₉₄O₉Si₃
• 分子量: 995.613
• InChiKey: ZRMMYVFWLKHMJB-ZGWQPKACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.47
• 重原子数：
  68.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,9S,13S,14S)-14-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-1-phenyl-hexadec-15-ene-1,5,11-trione 在 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 作用下， 生成 (2S,3R,9S)-10-[(2R,4S,5S,6S)-6-[(R)-3-Benzyloxy-2-(2-trimethylsilanyl-ethoxymethoxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-vinyl-tetrahydro-pyran-2-yl]-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-1-phenyl-decane-1,5-dione
  参考文献：
  名称：

  (+)-Rimocidin Synthetic Studies. Construction of an Advanced C(1−18) Polyol Fragment

  摘要：

  The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include the S(N)2/S(N)2' addition of dithiane anions to vinyl epoxides and the multicomponent linchpin union of 2-TBS-1,3-dithiane with two advanced epoxides.

  DOI：

  10.1021/ol034989g
• 作为产物：
  描述：

  tert-butyl-[(2R,3S)-1-[2-[(4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[2-[(2S,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,6R)-2,2-dimethyl-6-(phenylmethoxymethyl)-1,3-dioxan-4-yl]pent-4-enyl]-1,3-dithian-2-yl]pentyl]-1,3-dithian-2-yl]-3-(2-phenyl-1,3-dithian-2-yl)pentan-2-yl]oxy-dimethylsilane 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 水 为溶剂， 以67%的产率得到(2S,3R,9S,13S,14S)-14-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-1-phenyl-hexadec-15-ene-1,5,11-trione
  参考文献：
  名称：

  (+)-Rimocidin Synthetic Studies. Construction of an Advanced C(1−18) Polyol Fragment

  摘要：

  The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include the S(N)2/S(N)2' addition of dithiane anions to vinyl epoxides and the multicomponent linchpin union of 2-TBS-1,3-dithiane with two advanced epoxides.

  DOI：

  10.1021/ol034989g