(4S,5R,6R)-4-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxane | 383187-65-3

• 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: (4S,5R,6R)-4-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxane
• CAS: 383187-65-3
• 化学式: C₂₈H₄₀O₇
• 分子量: 488.621
• InChiKey: CKUHONZHIPVWNT-UGBRUMQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-4-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxane 在 lithium hydroxide 、 草酰氯 、 4 A molecular sieve 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 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
• 作为产物：
  描述：

  (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 氯代二环己基硼烷 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 溶剂黄146 、 乙腈 为溶剂， 反应 56.0h， 生成 (4S,5R,6R)-4-[(2S)-1-[(4-methoxyphenyl)methoxy]propan-2-yl]-2,2,5-trimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)-1,3-dioxane
  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.