tert-butyl N-[4-[(2R,6R)-4-methylidene-6-[[(2R,4S,6R)-6-(2-methyl-1,3-oxazol-4-yl)-4-tri(propan-2-yl)silyloxyoxan-2-yl]methyl]oxan-2-yl]but-2-ynoyl]-N-phenylcarbamate | 1264193-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[4-[(2R,6R)-4-methylidene-6-[[(2R,4S,6R)-6-(2-methyl-1,3-oxazol-4-yl)-4-tri(propan-2-yl)silyloxyoxan-2-yl]methyl]oxan-2-yl]but-2-ynoyl]-N-phenylcarbamate
• CAS: 1264193-96-5
• 化学式: C₄₀H₅₈N₂O₇Si
• 分子量: 706.995
• InChiKey: GLNIFGFAAOBOQZ-MLLXRYGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.62
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[(2R,6R)-4-methylidene-6-[[(2R,4S,6R)-6-(2-methyl-1,3-oxazol-4-yl)-4-tri(propan-2-yl)silyloxyoxan-2-yl]methyl]oxan-2-yl]but-2-ynoyl]-N-phenylcarbamate 在 lithium diisopropyl amide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以57%的产率得到(4-{(2R,6R)-6-[(2R,4S,6R)-6-(2-bromomethyloxazol-4-yl)-4-(triisopropylsilanyloxy)tetrahydropyran-2-ylmethyl]-4-methylenetetrahydropyran-2-yl}but-2-ynoyl)phenyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 Bis-pyran Unit of Phorboxazole B

  摘要：

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.

  DOI：

  10.1021/ol102860r
• 作为产物：
  描述：

  methyl (5R)-5-hydroxy-3-oxo-6-phenylmethoxyhexanoate 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 四氯化钛 、 苯基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二丁醚 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 147.17h， 生成 tert-butyl N-[4-[(2R,6R)-4-methylidene-6-[[(2R,4S,6R)-6-(2-methyl-1,3-oxazol-4-yl)-4-tri(propan-2-yl)silyloxyoxan-2-yl]methyl]oxan-2-yl]but-2-ynoyl]-N-phenylcarbamate
  参考文献：
  名称：

  The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 Bis-pyran Unit of Phorboxazole B

  摘要：

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.

  DOI：

  10.1021/ol102860r

文献信息

• The Asymmetric Maitland−Japp Reaction and Its Application to the Construction of the C1−C19 <i>Bis</i>-pyran Unit of Phorboxazole B
  作者：Paul A. Clarke、Soraia Santos、Nimesh Mistry、Laurence Burroughs、Alexander C. Humphries

  DOI：10.1021/ol102860r

  日期：2011.2.18

  The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.