7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin | 679398-77-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin
• CAS: 679398-77-7
• 化学式: C₃₅H₄₄O₁₄Si
• 分子量: 716.811
• InChiKey: LWYPHYQQBYYSTF-WZHGPVMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  179.42
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin 在 四丁基氟化铵 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 35.33h， 生成 apigenin-4'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

  摘要：

  We have succeeded in the first total synthesis of apigenin 7,4'-di-O-beta-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4'-OH of 12a with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3.Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement Of D-glucose at 7 and/or 4'-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-beta-glucosides (6a,b) and 4'-O-beta-glucosides (7a,b) also proved possible. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.001
• 作为产物：
  描述：

  柚皮素 在 咪唑 、 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 7-O-tert-butyldimethylsilyl-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)naringenin
  参考文献：
  名称：

  Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

  摘要：

  We have succeeded in the first total synthesis of apigenin 7,4'-di-O-beta-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4'-OH of 12a with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3.Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement Of D-glucose at 7 and/or 4'-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-beta-glucosides (6a,b) and 4'-O-beta-glucosides (7a,b) also proved possible. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.001