4-methoxy-cinnamyl O-β-D-glucopyranoside | 143729-77-5

• 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-methoxy-cinnamyl O-β-D-glucopyranoside
• 英文别名: 4-methoxy-cinnamyl-O-β-D-glucopyranoside；4-methoxycinnamyl β-D-glucopyranoside；vimalin；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-(4-methoxyphenyl)prop-2-enoxy]oxane-3,4,5-triol
• CAS: 143729-77-5
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: XRQSXJGKRJVWSU-FAOXUISGSA-N

物化性质

• 熔点：
  111.0-112.5 °C
• 沸点：
  584.2±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 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：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 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 、 copper diacetate 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-methoxy-cinnamyl 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

• Simple Synthesis of .BETA.-D-Glycopyranosides Using .BETA.-Glycosidase from Almonds
  作者：Katsumi Kurashima、Mikio Fujii、Yoshiteru Ida、Hiroyuki Akita

  DOI：10.1248/cpb.52.270

  日期：——

  Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,ω-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl β-D-glucopyranoside (5) using β-glucosidase from almonds stereoselectively gave the corresponding β-D-glucopyranosides in moderate yield.

  酶促糖苷化反应对二十一种醇类（正庚醇、正辛醇、2-苯乙醇、3-苯丙醇、4-苯丁醇、5-苯戊醇、6-苯己醇、呋喃醇、2-吡啶甲醇、异丁醇、异戊醇、对甲氧基肉桂醇）进行，其中包括次级醇（异丙醇、环己醇、1-苯乙醇）和1,ω-烷二醇（1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇），水杨醇及4-硝基苯基β-D-葡萄糖吡喃苷（5），使用来自杏仁的β-葡萄糖苷酶选择性地生成了相应的β-D-葡萄糖吡喃苷，产率适中。
• 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