(1R,2S,4R,6Z)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-(2-hydroxyethylidene)-1-(trimethylsilylmethyl)cyclohexan-1-ol | 1250265-33-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2S,4R,6Z)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-(2-hydroxyethylidene)-1-(trimethylsilylmethyl)cyclohexan-1-ol
• CAS: 1250265-33-8
• 化学式: C₂₄H₅₂O₄Si₃
• 分子量: 488.931
• InChiKey: GUOLSFOSXBMICE-YLHSAYAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,6Z)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-(2-hydroxyethylidene)-1-(trimethylsilylmethyl)cyclohexan-1-ol 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以0.301 g的产率得到[3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol
  参考文献：
  名称：

  Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃

  摘要：

  The A-rings of calcitriol (1 alpha,25-dihydeoxyvitamin D-3) and 1 alpha-hydroxy-3-deoxyvitamin D-3 were synthesized using the furan approach The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)-propanal. a diostereoselective Friedel-Crafts hydroxyalkylation an oxidation of the 2.3-disubstituted furan to give a gamma-hydroxybutenolide and a Peterson olefinatiion The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield

  DOI：

  10.1021/jo101155c
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (1R,2S,4R,6Z)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6-(2-hydroxyethylidene)-1-(trimethylsilylmethyl)cyclohexan-1-ol
  参考文献：
  名称：

  Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃

  摘要：

  The A-rings of calcitriol (1 alpha,25-dihydeoxyvitamin D-3) and 1 alpha-hydroxy-3-deoxyvitamin D-3 were synthesized using the furan approach The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)-propanal. a diostereoselective Friedel-Crafts hydroxyalkylation an oxidation of the 2.3-disubstituted furan to give a gamma-hydroxybutenolide and a Peterson olefinatiion The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield

  DOI：

  10.1021/jo101155c