(2R,5R,8R)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethyl-5-(tolyl-4-sulfonyl)oxocan-3-one | 219916-36-6

• 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,5R,8R)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethyl-5-(tolyl-4-sulfonyl)oxocan-3-one
• CAS: 219916-36-6
• 化学式: C₃₃H₄₂O₅SSi
• 分子量: 578.845
• InChiKey: FISPUJSGTAETJZ-UTRRVQLRSA-N

反应信息

• 作为反应物：
  描述：

  (2R,5R,8R)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethyl-5-(tolyl-4-sulfonyl)oxocan-3-one 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 25.33h， 生成 (2R,3R,8R)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(benzyloxy)-2-ethyl-3,4,7,8-tetrahydro-2H-oxocin
  参考文献：
  名称：

  Enantioselective Synthesis of α,β,α‘-Trisubstituted Cyclic Ethers

  摘要：

  A synthetic strategy for the preparation of trisusbstituted cyclic ethers is presented, in which the stereochemistry at the carbon atoms adjacent to the oxygen of the ether was controlled by means of a hetero Diels-Alder reaction between a monoactivated diene and a chiral aldehyde. The adducts were transformed into linear ethers, which were then used for the preparation of cis and trans cyclic ethers of different sizes. A cis-oxepane, cis-oxonane, and cis-oxocane and a trans-oxocane were prepared as examples of the scope of the strategy.

  DOI：

  10.1021/jo981188w
• 作为产物：
  描述：

  (R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-[(R)-1-hydroxymethyl-4-(toluene-4-sulfonyl)-butoxy]-propionic acid methyl ester 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 TEA 、 camphor-10-sulfonic acid 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 对甲苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 41.92h， 生成 (2R,5R,8R)-8-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethyl-5-(tolyl-4-sulfonyl)oxocan-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of α,β,α‘-Trisubstituted Cyclic Ethers

  摘要：

  A synthetic strategy for the preparation of trisusbstituted cyclic ethers is presented, in which the stereochemistry at the carbon atoms adjacent to the oxygen of the ether was controlled by means of a hetero Diels-Alder reaction between a monoactivated diene and a chiral aldehyde. The adducts were transformed into linear ethers, which were then used for the preparation of cis and trans cyclic ethers of different sizes. A cis-oxepane, cis-oxonane, and cis-oxocane and a trans-oxocane were prepared as examples of the scope of the strategy.

  DOI：

  10.1021/jo981188w