(2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one | 383187-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one
• 英文别名: (2R,3S,4S)-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methylphenyl)pentan-1-one
• CAS: 383187-47-1
• 化学式: C₂₅H₃₄O₇
• 分子量: 446.541
• InChiKey: XVSLGEOVELMQPP-JIGPKXGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-one 在 盐酸 、 lithium hydroxide 、 草酰氯 、 4 A molecular sieve 、 二甲基亚砜 、 三乙胺 、 对甲苯磺酰肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 tetramethylammonium triacetoxyborohydride 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 56.5h， 生成 (2R,3R,4S,5R,6R)-2-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methyl-phenyl)-tetrahydro-pyran-4-ol
  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：

  2',4'-二甲氧基-3'-甲基苯丙酮 在 三氟化硼-二甲醚络合物 、 potassium carbonate 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 47.75h， 生成 (2R,3S,4S)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-1-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.