(E,2R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxan-4-yl]hept-4-en-3-one | 383187-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,2R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxan-4-yl]hept-4-en-3-one
• CAS: 383187-77-7
• 化学式: C₄₁H₅₆O₇Si
• 分子量: 688.977
• InChiKey: AFRVNLVCNUIJEV-SXOJSOJTSA-N

物化性质

• 沸点：
  691.0±55.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E,2R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxan-4-yl]hept-4-en-3-one 在 盐酸 、 4 A molecular sieve 、 对甲苯磺酰肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis of the C1-C13 Fragment of Kendomycin: Atropisomerism around a C−Aryl Glycosidic Bond

  摘要：

  The left-hand fragment 2 of the novel antibiotic kendomycin (1) has been synthesized by an aldol addition and a Michael-type 1,4-addition of a C5 alcohol with a C9-C11 enone. Compound 2 shows an interesting atropisomerism around the C4a-C5-sp2 -sp3 bond. The atropisomers can be separated in pure forms by low-temperature high-pressure liquid chromatography.

  DOI：

  10.1002/1521-3773(20010903)40:17<3186::aid-anie3186>3.0.co;2-w
• 作为产物：
  描述：

  (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 lithium hydroxide 、 草酰氯 、 4 A molecular sieve 、 氯代二环己基硼烷 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 62.5h， 生成 (E,2R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-2-methyl-6-[(4S,5R,6R)-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxan-4-yl]hept-4-en-3-one
  参考文献：
  名称：

  Synthesis of the C1-C13 Fragment of Kendomycin: Atropisomerism around a C−Aryl Glycosidic Bond

  摘要：

  The left-hand fragment 2 of the novel antibiotic kendomycin (1) has been synthesized by an aldol addition and a Michael-type 1,4-addition of a C5 alcohol with a C9-C11 enone. Compound 2 shows an interesting atropisomerism around the C4a-C5-sp2 -sp3 bond. The atropisomers can be separated in pure forms by low-temperature high-pressure liquid chromatography.

  DOI：

  10.1002/1521-3773(20010903)40:17<3186::aid-anie3186>3.0.co;2-w

文献信息

• Synthesis of the C1-C13 Fragment of Kendomycin: Atropisomerism around a C−Aryl Glycosidic Bond
  作者：Harry J. Martin、Martina Drescher、Hanspeter Kählig、Sabine Schneider、Johann Mulzer

  DOI：10.1002/1521-3773(20010903)40:17<3186::aid-anie3186>3.0.co;2-w

  日期：2001.9.3

  The left-hand fragment 2 of the novel antibiotic kendomycin (1) has been synthesized by an aldol addition and a Michael-type 1,4-addition of a C5 alcohol with a C9-C11 enone. Compound 2 shows an interesting atropisomerism around the C4a-C5-sp2 -sp3 bond. The atropisomers can be separated in pure forms by low-temperature high-pressure liquid chromatography.