9-(tert-butyl-dimethyl-silanyloxy)-4-methyl-naphtho[2,3-b]furan-3-carboxylic acid benzyl ester | 950906-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 9-(tert-butyl-dimethyl-silanyloxy)-4-methyl-naphtho[2,3-b]furan-3-carboxylic acid benzyl ester
• 英文别名: Benzyl 9-[tert-butyl(dimethyl)silyl]oxy-4-methylbenzo[f][1]benzofuran-3-carboxylate
• CAS: 950906-66-8
• 化学式: C₂₇H₃₀O₄Si
• 分子量: 446.618
• InChiKey: NKDRCRGXDHTWSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(tert-butyl-dimethyl-silanyloxy)-4-methyl-naphtho[2,3-b]furan-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 四氯化钛 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.83h， 生成 ethyl (1R,15R)-1-methyl-8,13-dioxo-10,14-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,4,6,9(16),11-pentaene-15-carboxylate
  参考文献：
  名称：

  Furanosteroid Studies. Stereoselective Synthesis of the A,B,E-Ring Core of Wortmannin

  摘要：

  Alkyne oxazole 11c is converted in three steps, and similar to 45% overall yield, to furanolactone 21 alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CHO between C-3 and C-10 in furanoacid 14d is > 98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23 alpha,beta (dynamic kinetic resolution).

  DOI：

  10.1021/ol071158s
• 作为产物：
  描述：

  4-[2-(4-methyl-oxazole-5-carbonyl)-phenyl]-pent-2-ynoic acid benzyl ester 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 邻二甲苯 为溶剂， 反应 23.0h， 以76%的产率得到9-(tert-butyl-dimethyl-silanyloxy)-4-methyl-naphtho[2,3-b]furan-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Furanosteroid Studies. Stereoselective Synthesis of the A,B,E-Ring Core of Wortmannin

  摘要：

  Alkyne oxazole 11c is converted in three steps, and similar to 45% overall yield, to furanolactone 21 alpha having the A,B,E-ring core of the wortmannin (2) family of furanosteroids. The TiCl4-catalyzed insertion of EtO2C-CHO between C-3 and C-10 in furanoacid 14d is > 98% stereoselective via a pathway involving chemoselective lactonization of equilibrating aldol intermediates 23 alpha,beta (dynamic kinetic resolution).

  DOI：

  10.1021/ol071158s