tert-butyl (R)-2,2-dimethyl-4-[2,6-dichloro-3',5'-dimethoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate | 461031-87-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: tert-butyl (R)-2,2-dimethyl-4-[2,6-dichloro-3',5'-dimethoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate
• 英文别名: tert-butyl (4R)-4-(1,3-dichloro-8,10-dimethoxy-6-oxobenzo[c]chromen-2-yl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 461031-87-8
• 化学式: C₂₅H₂₇Cl₂NO₇
• 分子量: 524.398
• InChiKey: AFVUJEWGUMZNQD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2,2-dimethyl-4-[2,6-dichloro-3',5'-dimethoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 tert-butyl (P,R)-2,2-dimethyl-4-[(2,6-dichloro-4-hydroxy-3',5'-dimethoxy-1'-hydroxymethyl)-(3,2'-biphenyl)-1-yl]-oxazolidine-N-carboxylate 、 tert-butyl (P,R)-2,2-dimethyl-4-[(2,6-dichloro-4-hydroxy-3',5'-dimethoxy-1'-hydroxymethyl)-(3,2'-biphenyl)-1-yl]-oxazolidine-N-carboxylate
  参考文献：
  名称：

  On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin^,

  摘要：

  [GRAPHIC]Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.

  DOI：

  10.1021/ol026182e
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸甲酯 在 4-二甲氨基吡啶 、 palladium diacetate 、 sodium hydroxide 、 特戊酸钠 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 silver(I) iodide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、1.33 Pa 条件下， 反应 48.0h， 生成 tert-butyl (R)-2,2-dimethyl-4-[2,6-dichloro-3',5'-dimethoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate
  参考文献：
  名称：

  On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin^,

  摘要：

  [GRAPHIC]Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.

  DOI：

  10.1021/ol026182e

文献信息

• On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin^,
  作者：Gerhard Bringmann、Dirk Menche、Jörg Mühlbacher、Matthias Reichert、Nozomi Saito、Steven S. Pfeiffer、Bruce H. Lipshutz

  DOI：10.1021/ol026182e

  日期：2002.8.1

  [GRAPHIC]Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.