tert-butyl (R)-2,2-dimethyl-4-[3',5'-di-tert-butoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate | 461031-77-6

• 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-[3',5'-di-tert-butoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate
• 英文别名: tert-butyl (4R)-4-[8,10-bis[(2-methylpropan-2-yl)oxy]-6-oxobenzo[c]chromen-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 461031-77-6
• 化学式: C₃₁H₄₁NO₇
• 分子量: 539.669
• InChiKey: KIBPNDHAFWGZJQ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 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-[3',5'-di-tert-butoxy-6H-dibenzo[b,d]pyran-7'-on]-oxazolidine-N-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 异丙醇 为溶剂， 反应 0.17h， 生成 tert-butyl (P,R)-2,2-dimethyl-4-[(4-hydroxy-3',5'-di-tert-butoxy-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：

  3,5-二羟基苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 sodium acetate 、 氢气 、 2,4-滴二甲胺盐 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 tert-butyl (R)-2,2-dimethyl-4-[3',5'-di-tert-butoxy-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.