tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate | 150849-75-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate
• CAS: 150849-75-5
• 化学式: C₂₁H₃₂O₅S
• 分子量: 396.548
• InChiKey: WMCDQTWLVWEGJX-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate 在 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到(4S,5R)-4-(1,1-Dimethyl-2-phenylsulfanyl-ethyl)-6-iodomethyl-5-methoxymethoxy-[1,3]dioxan-2-one
  参考文献：
  名称：

  Iodine monobromide (IBr) at low temperature: A superior protocol for diastereoselective cyclizations of homoallylic carbonates

  摘要：

  Iodine monobromide (IBr) induces efficient electrophilic cyclizations of homoallylic t-butyl carbonates in toluene or methylene chloride al low temperature, affording significantly better diastereoselectivity than iodine (I2) in acetonitrile.

  DOI：

  10.1016/s0040-4039(00)79009-5
• 作为产物：
  描述：

  3-(甲氧基甲氧基)丙-1-烯 在 正丁基锂 作用下， 生成 tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate
  参考文献：
  名称：

  Iodine monobromide (IBr) at low temperature: enhanced diastereoselectivity in electrophilic cyclizations of homoallylic carbonates

  摘要：

  Iodine monobromide affords superior diastereoselectivity in low-temperature electrophilic cyclizations of homoallylic carbonates. Solvent and temperature effects and the scope and limitations of the method are discussed; optimal selectivity is obtained in toluene at -80 to -85-degrees-C. The latter protocol generally furnishes significantly enhanced selectivity, vis-a-vis the original procedure employing 12 in acetonitrile at -20-degrees-C; for example, the IBr-induced cyclization of 14 affords a 25.8:1 mixture of 15 and 16, whereas I2 gives an 8.4:1 ratio. An equilibration experiment established that the diastereoselectivity derives primarily or exclusively from kinetic control of the cyclization process.

  DOI：

  10.1021/jo00066a024

文献信息

• Iodine monobromide (IBr) at low temperature: A superior protocol for diastereoselective cyclizations of homoallylic carbonates
  作者：James J.-W. Duan、Paul A. Sprengeler、Amos B. Smith

  DOI：10.1016/s0040-4039(00)79009-5

  日期：1992.10

  Iodine monobromide (IBr) induces efficient electrophilic cyclizations of homoallylic t-butyl carbonates in toluene or methylene chloride al low temperature, affording significantly better diastereoselectivity than iodine (I2) in acetonitrile.
• Iodine monobromide (IBr) at low temperature: enhanced diastereoselectivity in electrophilic cyclizations of homoallylic carbonates
  作者：James J. W. Duan、Amos B. Smith

  DOI：10.1021/jo00066a024

  日期：1993.7

  Iodine monobromide affords superior diastereoselectivity in low-temperature electrophilic cyclizations of homoallylic carbonates. Solvent and temperature effects and the scope and limitations of the method are discussed; optimal selectivity is obtained in toluene at -80 to -85-degrees-C. The latter protocol generally furnishes significantly enhanced selectivity, vis-a-vis the original procedure employing 12 in acetonitrile at -20-degrees-C; for example, the IBr-induced cyclization of 14 affords a 25.8:1 mixture of 15 and 16, whereas I2 gives an 8.4:1 ratio. An equilibration experiment established that the diastereoselectivity derives primarily or exclusively from kinetic control of the cyclization process.