(2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-4-ol | 294203-73-9

• 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: (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-4-ol
• CAS: 294203-73-9
• 化学式: C₄₉H₅₂O₇Si
• 分子量: 781.033
• InChiKey: MGPLJHFBHVNOAN-HENRPQKXSA-N

物化性质

• 沸点：
  823.2±65.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.56
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-4-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以32%的产率得到(2R,3R)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

  摘要：

  A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2AgClO4, and subsequent oxidation of the C(4) position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00826-1
• 作为产物：
  描述：

  (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 在 咪唑 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-4-ol
  参考文献：
  名称：

  First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

  摘要：

  A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2AgClO4, and subsequent oxidation of the C(4) position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00826-1

文献信息

• Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-benzyl-(+)-catechin and (−)-epicatechin as a key building monomer
  作者：Kin-ichi Oyama、Miyuki Kuwano、Mie Ito、Kumi Yoshida、Tadao Kondo

  DOI：10.1016/j.tetlet.2008.02.173

  日期：2008.5

  3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3',4'-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of la in the presence of a catalytic amount of B(C6F5)(3) afforded wide-range procyanidins from dimer to 15-mer like a biomass. (C) 2008 Elsevier Ltd. All rights reserved.
• First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine
  作者：Ken Ohmori、Hiroki Ohrui、Keisuke Suzuki

  DOI：10.1016/s0040-4039(00)00826-1

  日期：2000.7

  A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2AgClO4, and subsequent oxidation of the C(4) position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: glycoside–flavonoid analogy
  作者：Ken Ohmori、Keisuke Hatakeyama、Hiroki Ohrui、Keisuke Suzuki

  DOI：10.1016/j.tet.2003.08.076

  日期：2004.2

  Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for S(N)1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.