(R)-3-<(tert-Butyldimethylsilyl)oxy>-1,1-dibromo-1-butene | 171011-69-1

• 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: (R)-3-<(tert-Butyldimethylsilyl)oxy>-1,1-dibromo-1-butene
• 英文别名: tert-butyl-[(2R)-4,4-dibromobut-3-en-2-yl]oxy-dimethylsilane
• CAS: 171011-69-1
• 化学式: C₁₀H₂₀Br₂OSi
• 分子量: 344.162
• InChiKey: SXXAYTUOMLBKBN-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-3-<(tert-Butyldimethylsilyl)oxy>-1,1-dibromo-1-butene 在 甲基溴化镁 作用下， 生成 (R)-(but-3-yn-2-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  实用合成手性炔丙醇

  摘要：

  从廉价且容易获得的手性乳酸甲酯开始，开发了一种实用且有效的手性炔丙醇的合成方法。另外，发现了区域选择性的甲硅烷基化方法用于具有末端三甲基甲硅烷基的双甲硅烷基化的炔醇的氧脱保护。

  DOI：

  10.1016/0040-4039(95)00384-o
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 (R)-3-<(tert-Butyldimethylsilyl)oxy>-1,1-dibromo-1-butene
  参考文献：
  名称：

  Synthesis of a C22-34 Subunit of the Immunosuppressant FK-506

  摘要：

  A new route to the C22-34 subunit of FK-506 was developed. A highly diastereoselective Diels-Alder reaction of 1,3-butadiene with the bis-acrylate of (R,R)-hydrobenzoin and subsequent saponification provided the cyclohexenecarboxylic acid 6.4 of 95% ee. Elaboration to the enal 9.2 was effected by known transformations. Enal 9.2 underwent diastereoselective and enantiospecific S(E)2' addition of allenyl stannane (S)-3.9 affording the homopropargylic alcohol 9.3 as an 85:15 syn/anti mixture. The PMB ether 9.5 was converted to the known benzylidene derivative 10.4 by sequential treatment with Red-Al, epoxidation, a second reduction with Red-Al, and oxidative benzylidene formation with DDQ.

  DOI：

  10.1021/jo00127a031

文献信息

• Synthesis of a C22-34 Subunit of the Immunosuppressant FK-506
  作者：James A. Marshall、Shiping Xie

  DOI：10.1021/jo00127a031

  日期：1995.11

  A new route to the C22-34 subunit of FK-506 was developed. A highly diastereoselective Diels-Alder reaction of 1,3-butadiene with the bis-acrylate of (R,R)-hydrobenzoin and subsequent saponification provided the cyclohexenecarboxylic acid 6.4 of 95% ee. Elaboration to the enal 9.2 was effected by known transformations. Enal 9.2 underwent diastereoselective and enantiospecific S(E)2' addition of allenyl stannane (S)-3.9 affording the homopropargylic alcohol 9.3 as an 85:15 syn/anti mixture. The PMB ether 9.5 was converted to the known benzylidene derivative 10.4 by sequential treatment with Red-Al, epoxidation, a second reduction with Red-Al, and oxidative benzylidene formation with DDQ.
• A practical synthesis of chiral propargylic alcohols
  作者：Yi-Yin Ku、Ramesh R. Patel、E Michael Elisseou、David P. Sawick

  DOI：10.1016/0040-4039(95)00384-o

  日期：1995.4

  chiral propargylic alcohols has been developed starting from inexpensive and readily available chiral methyl lactate. In addition, a regioselective desilylation method was discovered for oxygen deprotection of bis-silylated alkynols having a terminal trimethylsilyl group.

  从廉价且容易获得的手性乳酸甲酯开始，开发了一种实用且有效的手性炔丙醇的合成方法。另外，发现了区域选择性的甲硅烷基化方法用于具有末端三甲基甲硅烷基的双甲硅烷基化的炔醇的氧脱保护。