(3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-3,4-epoxy-6-methyl-1-heptene | 217434-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-3,4-epoxy-6-methyl-1-heptene
• 英文别名: tert-butyl N-[(1S)-1-[(2S,3R)-3-ethenyloxiran-2-yl]-2-methylpropyl]carbamate
• CAS: 217434-50-9
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: FUPFIBHYJKGEDH-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-3,4-epoxy-6-methyl-1-heptene 在 sodium perborate 、 bis(cyclohexanyl)borane 作用下， 生成 {(S)-1-[(2S,3R)-3-(2-Hydroxy-ethyl)-oxiranyl]-2-methyl-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  An efficient approach to chiral cis-3,4-epoxy alcohols

  摘要：

  A new method for the synthesis of cis-3,4-epoxy alcohols has been developed by employing hydroboration of chiral cis-vinylepoxides or syn-chlorohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01773-0
• 作为产物：
  描述：

  N-BOC-2(S)-2-AMINO-3-METHYL-BUTAL聽 在 ^dIpc₂BOMe 、 三氟化硼乙醚 、 lithium dicyclohexylamide 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 (3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-3,4-epoxy-6-methyl-1-heptene
  参考文献：
  名称：

  Diastereoselective Chloroallylboration of α-Chiral Aldehydes

  摘要：

  Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-17) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent diatereoselectivity (greater than or equal to 90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.

  DOI：

  10.1021/jo980977a

文献信息

• Diastereoselective Chloroallylboration of α-Chiral Aldehydes
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo980977a

  日期：1998.11.1

  Double asymmetric reaction of chiral (Z)-(gamma-chloroallyl)borane, 2, with alpha-chiral aldehydes (3-7) provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins (8-17) and vinyl epoxides(18-27). Both enantiomers of 2 exhibited excellent diatereoselectivity (greater than or equal to 90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity.
• An efficient approach to chiral cis-3,4-epoxy alcohols
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1016/s0040-4039(98)01773-0

  日期：1998.10

  A new method for the synthesis of cis-3,4-epoxy alcohols has been developed by employing hydroboration of chiral cis-vinylepoxides or syn-chlorohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.