3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside | 113349-27-2

• 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: 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside
• 英文别名: 4-hydroxy-3-methoxycinnamyl β-D-glucopyranoside；4-hydroxy-3-methoxycinnamyl-β-D-glucopyranoside；(E)-coniferyl alcohol 9-O-β-glucopyranoside；trans-isoconiferin；(E)-isoconiferin；isoconiferin；Citrusin D；(2R,3R,4S,5S,6R)-2-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 113349-27-2
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: JOIDTHZGWZZGMU-FAOXUISGSA-N

物化性质

• 沸点：
  606.9±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

制备方法与用途

异绿原酸是由香草醛、丁香醛和对羟基苯甲醛经过五个反应步骤合成的一种化合物，总收率较高。

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside 在 sodium phosphate-citrate buffer 、 β-glucosidase 作用下， 反应 24.0h， 生成 反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇
  参考文献：
  名称：

  Derivatives of unsaturated aromatic alcohols in propolis and styrax benzoin

  摘要：

  DOI：

  10.1007/bf00579470
• 作为产物：
  描述：

  D-葡萄烯糖 在 4-二甲氨基吡啶 、 2,2-dimethyldioxirane 、 3 A molecular sieve 、 Amberlite IRA₄₀₀ (OH^-) 、 4-甲基苯磺酸吡啶 、 silica gel 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 苯 为溶剂， 反应 115.0h， 生成 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside
  参考文献：
  名称：

  Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose

  摘要：

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10315-x

文献信息

• A selective and mild glycosylation method of natural phenolic alcohols
  作者：Mária Mastihubová、Monika Poláková

  DOI：10.3762/bjoc.12.51

  日期：——

  Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ–iodine or ZnO–ZnCl₂ catalyst combination. Among them, ZnO–iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

  几种生物活性的天然p-羟基苯丙基β-D-葡萄糖苷，如香草基β-D-葡萄糖苷、沙利度苷和异云杉醇苷，以及它们的糖苷类似物，通过简单的反应序列制备。通过利用乙酰化的葡萄糖溴化物以及芳香基团和温和的糖苷化促进剂，实现了高效的合成方法。去糖基物质p-O-乙酰化芳基丙基醇是通过还原相应的乙酰化醛或酸制备的。研究了各种立体选择性的1,2-trans-O-糖基化方法，包括DDQ-碘或ZnO-ZnCl2催化剂组合。其中，ZnO-碘已被确认为一种新的糖苷化促进剂，并成功应用于立体选择性糖苷合成。最终产品通过传统的Zemplén去乙酰化获得。
• 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 preparation of phenylpropenoid β-d-glucopyranoside congeners by Mizoroki–Heck type reaction using organoboron reagents
  作者：Masashi Kishida、Hiroyuki Akita

  DOI：10.1016/j.tet.2005.08.043

  日期：2005.10

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

  DOI：——

  日期：——
• Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-d-glucopyranose
  作者：Yoh-ichi Matsushita、Kazuhiro Sugamoto、Yoshio Kita、Takanao Matsui

  DOI：10.1016/s0040-4039(97)10315-x

  日期：1997.12

  1,2-Anhydro-3,4,6-tri-O-pivaloyl-alpha-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford beta-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present reaction. (C) 1997 Elsevier Science Ltd.