(2R)-4-(tert-butyldimethylsilyloxy)-1-(3-furyl)butan-2-ol | 1250265-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R)-4-(tert-butyldimethylsilyloxy)-1-(3-furyl)butan-2-ol
• 英文别名: (2R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(furan-3-yl)butan-2-ol
• CAS: 1250265-26-9
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: KAXWAMXWPNLNML-ZDUSSCGKSA-N

物化性质

• 沸点：
  327.0±37.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-4-(tert-butyldimethylsilyloxy)-1-(3-furyl)butan-2-ol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.55h， 以96%的产率得到(3R)-1,3-bis(tert-butyldimethylsilyloxy)-4-(3-furyl)butane
  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：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 呋喃,2,3-二氢-3-亚甲基- 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 乙醚 为溶剂， 反应 0.38h， 以78%的产率得到(2R)-4-(tert-butyldimethylsilyloxy)-1-(3-furyl)butan-2-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

文献信息

• Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃
  作者：William H. Miles、Katelyn B. Connell、Gözde Ulas、Hannah H. Tuson、Elizabeth A. Dethoff、Varun Mehta、April J. Thrall

  DOI：10.1021/jo101155c

  日期：2010.10.15

  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