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 | 585535-27-9

• 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: 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
• CAS: 585535-27-9
• 化学式: C₆₅H₁₁₂O₆S₆Si₃
• 分子量: 1266.25
• InChiKey: BLNSAMWYHJZUKO-JEOIMGBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.31
• 重原子数：
  80
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  207
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (2S)-1-[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]-5-[2-[(2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(2-phenyl-1,3-dithian-2-yl)pentyl]-1,3-dithian-2-yl]pentan-2-ol 在 2,6-二甲基吡啶 作用下， 以80%的产率得到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
  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

文献信息

• (+)-Rimocidin Synthetic Studies: Construction of the C(1−27) Aglycone Skeleton
  作者：Amos B. Smith、Megan A. Foley、Shuzhi Dong、Alia Orbin

  DOI：10.1021/jo900765p

  日期：2009.8.21

  Assembly of the C(1−27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the SN2/SN2′ reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1−19) carbon backbone

  雷莫西丁内酯（(+)-雷莫西丁 ( 1 ) 的糖苷配基）的 C(1−27) 大环骨架的组装已以收敛方式实现。该合成策略的主要特点是应用多组分 I 型阴离子中继化学 (ARC)，结合乙烯基环氧化物的S N 2/S N 2' 反应流形，两者均采用 2-取代 1,3-二噻烷来构建C(1−19) 碳主链。具有全反式三烯的 C(20−27) 硼酸乙烯基酯与先进的 C(1−19) 乙烯基碘化物的 Yamaguchi 结合，然后通过 Suzuki−Miyaura 交叉偶联进行大环化，完成了 C(1− 27)利莫西内酯骨架。