(3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)oxan-2-yl]-3-methylbutan-2-one | 383187-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)oxan-2-yl]-3-methylbutan-2-one
• CAS: 383187-78-8
• 化学式: C₃₈H₅₂O₇Si
• 分子量: 648.912
• InChiKey: IAGYUPKIACNYOJ-LHUKGKGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)oxan-2-yl]-3-methylbutan-2-one 在 4 A molecular sieve 、 对甲苯磺酰肼 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以65%的产率得到(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：

  (S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one 在 盐酸 、 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 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 68.5h， 生成 (3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5-trimethoxy-4-methylphenyl)oxan-2-yl]-3-methylbutan-2-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.