[(S)-1-((1S,2R)-2-Hydroxy-1-hydroxymethyl-3,3-dimethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester | 188659-45-2

• 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: [(S)-1-((1S,2R)-2-Hydroxy-1-hydroxymethyl-3,3-dimethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(2S,3R)-1,3-dihydroxy-4,4-dimethylhex-5-en-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 188659-45-2
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: JJGQSZZDGHFJHM-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-1-((1S,2R)-2-Hydroxy-1-hydroxymethyl-3,3-dimethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester 在 二甲基硫 、 臭氧 作用下， 生成 [(S)-1-((3S,4R)-4,6-Dihydroxy-5,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Barbier-type allylation of chiral α-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

  摘要：

  The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00050-1
• 作为产物：
  描述：

  benzyl N-[(2S)-1-[[(2S)-1-hydroxy-3-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate 、 1-溴-3-甲基-2-丁烯 在 tin 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 [(S)-1-((1S,2S)-2-Hydroxy-1-hydroxymethyl-3,3-dimethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester 、 [(S)-1-((1S,2R)-2-Hydroxy-1-hydroxymethyl-3,3-dimethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Barbier-type allylation of chiral α-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide

  摘要：

  The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00050-1

文献信息

• Barbier-type allylation of chiral α-aminoaldehydes: Dependence of the stereochemical outcome on metal and allylic halide
  作者：Frank Rübsam、Stephan Seck、Athanassios Giannis

  DOI：10.1016/s0040-4020(97)00050-1

  日期：1997.2

  The chiral beta-hydroxy-alpha-aminoaldehydes of type 1 react smoothly with allyl-, 3,3-dimethylallyl bromide and 2-bromo-cyclohexene in the presence of tin or zinc dust to give the homoallylic alcohols of type 3. For the first time it is shown that the diastereoselectivity in in the Barbier reaction can be influenced by the choice of metal and/or allylic halide. (C) 1997 Published by Elsevier Science Ltd.