4-hydroxycinnamyl alcohol 9-O-β-D-glucopyranoside | 132294-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxycinnamyl alcohol 9-O-β-D-glucopyranoside
• 英文别名: p-coumaryl alcohol-γ-O-β-D-glucopyranoside；4-hydroxy-cinnamyl-O-β-D-glucopyranoside；4-hydroxylcinnamyl-O-β-D-glucopyranoside；4-hydroxycinnamyl O-β-D-glucopyranoside；4-hydroxycinnamyl-O-β-D-glucopyranoside；4-hydroxycinnamyl β-D-glucopyranoside；Sachaliside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-(4-hydroxyphenyl)prop-2-enoxy]oxane-3,4,5-triol
• CAS: 132294-76-9
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: CNNXMGXBAZQZDE-HHMSBIESSA-N

物化性质

• 熔点：
  118-123 °C
• 沸点：
  590.2±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-hydroxycinnamyl alcohol 9-O-β-D-glucopyranoside 生成 4-(3-羟基丙-1-烯基)苯酚
  参考文献：
  名称：

  SOKOLOV, S. YA.;BOJKO, V. P.;KURKIN, V. A.;ZAPESOCHNAYA, G. G.;RVANTSOVA,+, XIM.-FARMATS. ZH., 24,(1990) N0, S. 66-68

  摘要：

  DOI：
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 在 lithium acetate 、 sodium methylate 、 copper diacetate 、 palladium diacetate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-hydroxycinnamyl alcohol 9-O-β-D-glucopyranoside
  参考文献：
  名称：

  Simple preparation of phenylpropenoid β-d-glucopyranoside congeners by Mizoroki–Heck type reaction using organoboron reagents

  摘要：

  Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-beta-(D)-glucopyranoside (3) and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- beta-(D)-glucopyranosides (4a-m) in good yield. Among them, coupling products 4a-m were converted to not only the naturally occurring phenylpropenoid beta-(D)-glucopyranoside analogues (la-e) but also the unnaturally ones (If-m). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.043

文献信息

• A Sustainable One‐Pot, Two‐Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
  作者：Ivan Bassanini、Jana Krejzová、Walter Panzeri、Daniela Monti、Vladimir Křen、Sergio Riva

  DOI：10.1002/cssc.201700136

  日期：2017.5.9

  A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus

  开发了一种可持续，方便，可扩展，一锅二酶的芳基烷基醇糖基化方法。该反应方案是基于从由rutinosidase催化的transrutinosylation黑曲霉使用便宜的市售的天然类黄酮芦丁为糖基供体，然后进行选择性“微调”通过从鼠李糖苷酶催化的芸香糖苷单元的土曲霉。该过程已通过几种天然生物活性葡萄糖苷的合成得到验证，无需硅胶色谱法，可以分离出高达75％的收率。
• Simple synthesis of phenylpropenoid β-d-glucopyranoside congeners based on Mizoroki–Heck type reaction of organoboron reagents
  作者：Masashi Kishida、Hiroyuki Akita

  DOI：10.1016/j.tetlet.2005.04.023

  日期：2005.6

  Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (3) and phenylboronic acid congeners gave the phenylpropenoid 2,3,4,6-tetra-O-acetyl-beta-D-glueopyranoside (4a-f) in good.yield. Among them, compounds 4a-c were converted to the naturally occurring phenylpropenoid beta-D-glucopyranoside analogues (1a-c). (c) 2005 Elsevier Ltd. All rights reserved.
• Phenylpropanoids of a callus culture of Rhodiola rosea
  作者：V. A. Kurkin、G. G. Zapesochnaya、A. G. Dubichev、E. D. Vorontsov、I. V. Aleksandrova、R. V. Panova

  DOI：10.1007/bf00636560

  日期：1991.7
• ROTHEN, LAURE;SCHLOSSER, MANFRED, TETRAHEDRON LETT., 32,(1991) N2, C. 2475-2476
  作者：ROTHEN, LAURE、SCHLOSSER, MANFRED

  DOI：——

  日期：——