(+)-syringaresinol O-β-D-glucopyranoside pentaacetate

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: (+)-syringaresinol O-β-D-glucopyranoside pentaacetate
• 英文别名: [(2R,3R,4S,5R,6S)-6-[4-[(3S,3aR,6S,6aR)-6-(4-acetyloxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• 化学式: C₃₈H₄₆O₁₈
• 分子量: 790.772
• InChiKey: BKLUEPLPMYEHOD-DAIISBFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  56
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  205
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (+)-syringaresinol O-β-D-glucopyranoside pentaacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以87%的产率得到刺五加提取物
  参考文献：
  名称：

  Synthesis of biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)- mono- and bis-glucosides

  摘要：

  The naturally occurring tetrahydrofurofuran-lignan-(syringaresinol, pinoresinol)-mono- and bis-glucosides were synthesized and their structures thereby confirmed.

  DOI：

  10.1016/s0031-9422(00)98258-x
• 作为产物：
  描述：

  反式芥子醇 在 吡啶 、 氢氧化钾 、 air 、 copper(II) sulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 49.5h， 生成 (+)-syringaresinol O-β-D-glucopyranoside pentaacetate
  参考文献：
  名称：

  Synthesis of biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)- mono- and bis-glucosides

  摘要：

  The naturally occurring tetrahydrofurofuran-lignan-(syringaresinol, pinoresinol)-mono- and bis-glucosides were synthesized and their structures thereby confirmed.

  DOI：

  10.1016/s0031-9422(00)98258-x

文献信息

• The constituents of Eucommia ulmoides OLIV. II. Isolation and structures of three new lignan glycosides.
  作者：TAKESHI DEYAMA、TAKAKO IKAWA、SANSEI NISHIBE

  DOI：10.1248/cpb.33.3651

  日期：——

  Three new lignan glycosides were isolated from the bark of Eucommia ulmoides OLIV. (Eucommiaceae). Their structures were established as (-)-olivil 4', 4"-di-O-β-D-glucopyranoside (1), (+)-1-hydroxypinoresinol 4', 4"-di-O-β-D-glucopyranoside (2) and (+)-medioresinol 4'-O-β-D-glucopyranoside (named eucommin A) (3), based on chemical evidence and spectroscopic studies. A known lignan glycoside, (+)-syringaresinol O-β-D-glucopyranoside (4) was also isolated.

  从杜仲（Eucommia ulmoides OLIV.(杜仲科）树皮中分离出三种新的木质素苷。根据化学证据和光谱研究，它们的结构被确定为(-)-olivil 4'，4"-di-O-β-D-吡喃葡萄糖苷（1）、(+)-1-hydroxypinoresinol 4'，4"-di-O-β-D-吡喃葡萄糖苷（2）和(+)-medioresinol 4'-O-β-D-吡喃葡萄糖苷（命名为杜仲素 A）（3）。此外，还分离出一种已知的木质素苷，(+)-syringaresinol O-β-D-glucopyranoside（4）。
• Studies on the constituents of Cistanchis Herba. V. Isolation and structures of two new phenylpropanoid glycosides, cistanosides E and F.
  作者：HIROMI KOBAYASHI、HIROKO KARASAWA、TOSHIO MIYASE、SEIGO FUKUSHIMA

  DOI：10.1248/cpb.33.1452

  日期：——

  Two new phenylpropanoid glycosides, named cistanosides E (III) and F (IV), were isolated from Cistanchis Herba, the whole plant of Cistanche salsa (C. A. MEY.) G. BECK (Orobanchaceae), together with two known lignan glycosides, liriodendrin (I) and (+)-syringaresinol O-β-D-glucopyranoside (II). The structures of III and IV were determined to be 2-(4-hydroxy-3-methoxyphenyl) ethyl O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranoside and α-L-rhamnopyranosyl (1→3)-O-(4-O-caffeoyl)-D-glucopyranose, respectively, on the basis of chemical and spectral data.

  从列当科肉苁蓉 (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (C. A. MEY.) G. BECK (列当科) 的全草中分离得到两种新的苯丙素苷，命名为肉苁蓉苷 E (III) 和 F (IV)。 I) 和 (+)-丁香树脂醇 O-β-D-吡喃葡萄糖苷 (II)。 III和IV的结构确定为2-(4-羟基-3-甲氧基苯基)乙基O-α-L-吡喃鼠李糖基-(1→3)-O-β-D-吡喃葡萄糖苷和α-L-吡喃鼠李糖基( 1→3)-O-(4-O-咖啡酰基)-D-吡喃葡萄糖，分别基于化学和光谱数据。
• Synthesis of biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)- mono- and bis-glucosides
  作者：Barbara Vermes、Otto Seligmann、Hildebert Wagner

  DOI：10.1016/s0031-9422(00)98258-x

  日期：1991.1

  The naturally occurring tetrahydrofurofuran-lignan-(syringaresinol, pinoresinol)-mono- and bis-glucosides were synthesized and their structures thereby confirmed.