(RS)-1-phenylethyl β-D-glucopyranoside | 101470-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-1-phenylethyl β-D-glucopyranoside
• 英文别名: 1-β-D-glucopyranosyloxy-1-phenylethane；1-phenylethyl β-D-glucopyranoside；1-Phenylethyl beta-D-glucoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1-phenylethoxy)oxane-3,4,5-triol
• CAS: 101470-15-9
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: FVJSVPNFQKQHOB-FRVCJKFISA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (RS)-1-phenylethyl β-D-glucopyranoside 在 phosphate buffer 、 almond-β-glucosidase 、 三氟化硼乙醚 、 potassium carbonate 、 四甲基胍 作用下， 以 水 、 乙腈 为溶剂， 反应 26.0h， 生成 1S-phenylethyl α-D-glucopyranoside
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022
• 作为产物：
  描述：

  苏合香醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 phosphate buffer 、 β-glucosidase 作用下， 反应 32.0h， 以12%的产率得到(RS)-1-phenylethyl β-D-glucopyranoside
  参考文献：
  名称：

  Simple Synthesis of .BETA.-D-Glycopyranosides Using .BETA.-Glycosidase from Almonds

  摘要：

  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。

  DOI：

  10.1248/cpb.52.270

文献信息

• Biotransformation of Benzaldehyde-Type and Acetophenone-Type Derivatives by Pharbitis nil Hairy Roots
  作者：Hideki Kanho、Sayaka Yaoya、Nobuo Kawahara、Takahisa Nakane、Yoichi Takase、Kazuo Masuda、Masanori Kuroyanagi

  DOI：10.1248/cpb.53.361

  日期：——

  The glucosylation of some coumarin and flavone derivatives on incubation with the hairy roots of morning glory (Pharbitis nil) was previously reported. We further studied the biotransformation of benzaldehyde- and acetophenone-type derivatives. Vanillin and isovanillin were reduced to alcoholic derivatives and glucosylated at the phenolic and the alcoholic hydroxyl groups. In the case of 3,4-dihydroxybenzaldehyde, the formyl group was reduced and the 3-hydroxyl or 4-hydroxyl groups were glucosylated to give monoglucosides. The 3-hydroxyl group was predominantly glucosylated to the 4-hydroxyl group. 4-β-D-Glucopyranosyloxy-3-methoxybenzylalcohol was obtained in low yield. In time-course experiments with vanillin, it was found that the high-level reduction of the formyl group and glucosylation of the phenolic hydroxyl group occurred, and finally 4-O-β-D-glucopyranosylvanillylalcohol was obtained as the main product. In the case of 3,4-dimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, and salicylaldehyde, the formyl groups were reduced, and then the hydroxyl groups at the benyl position were glucosylated to give alcoholic glucosides in relatively high yields. In 4-hydroxy-3-methoxyacetophenone, the 4-hydroxyl group was glucosylated and two dimerized glucosides, biphenyl and biphenylether types, were obtained in low yields. In acetophenone, 1-β-D-glucopyranosyloxy-1-phenylethane and 2-β-D-glucopyranosyloxyacetophenone were obtained. As mentioned above P. nil hairy roots showed various biotransformative activities including glucosylation of phenolic and benzylic hydroxyl groups, reduction of the formyl group near the benzene ring, and phenol oxidation dimerization. The glucosylation reaction was especially interesting for the production of valuable glucosides.

  之前已有研究报告显示，某些香豆素和黄酮衍生物在与牵牛花毛根（Pharbitis nil）孵育时发生了葡萄糖化反应。我们进一步研究了苯甲醛和乙酰苯酮类衍生物的生物转化。香草醛和异香草醛被还原为醇类衍生物，并分别在酚羟基和醇羟基上发生了葡萄糖化。在3,4-二羟基苯甲醛的情况下，甲醛基被还原，而3-羟基或4-羟基则被葡萄糖化，从而生成单糖苷。3-羟基主要葡萄糖化为4-羟基。4-β-D-葡萄糖吡喃酯氧基-3-甲氧基苄醇的产率较低。在与香草醛的时间过程实验中，发现甲醛基的高水平还原和酚羟基的葡萄糖化同时发生，最终获得了4-O-β-D-葡萄糖吡喃醇香草醇作为主要产物。在3,4-二甲氧基苯甲醛、3,4,5-三甲氧基苯甲醛和水杨醛的情况下，甲醛基被还原后，苄位的羟基被葡萄糖化，生成的醇类葡萄糖苷的产率相对较高。在4-羟基-3-甲氧基乙酰苯酮中，4-羟基被葡萄糖化，并生成了两种二聚葡萄糖苷，即联苯和联苯醚类，产率较低。在乙酰苯酮中，得到1-β-D-葡萄糖吡喃酯氧基-1-苯乙烯和2-β-D-葡萄糖吡喃酯氧基乙酰苯酮。如上所述，P. nil毛根显示了多种生物转化活性，包括酚羟基和苄羟基的葡萄糖化、苯环附近甲醛基的还原以及酚氧化二聚化。葡萄糖化反应尤其值得关注，因为它能够产生有价值的葡萄糖苷。
• Diastereoselective Formation of Disaccharides from (<b><i>RS</i></b>)-1-Phenylethanol by Cultured Cells of<b><i>Catharanthus roseus</i></b>
  作者：Toshifumi Hirata、Kei Shimoda、Takeshi Fujino、Shin-ya Yamane、Shinji Ohta

  DOI：10.1246/bcsj.74.539

  日期：2001.3

  The biotransformation of (RS)-1-phenylethanol with cultured cells of Catharanthus roseus gave its vicianoside [α-L-arabinopyranosyl-(1-6)-β-D-glucopyranoside], primeveroside [β-D-xylopyranosyl-(1-6)-β-D-glucopyranoside] and gentiobioside [β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside] via the corresponding glucoside. It was found that primeveroside and gentiobioside were enantioselectively composed of only (R)-1-phenylethanol as its aglycone moiety.

  用培养的长春花细胞对（RS）-1-苯乙醇进行生物转化，可以得到维基苷[α-L-阿拉伯呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]、初花苷[β-D-木糖呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]和绒毛苷[β-D-葡萄糖呋喃糖-(1-6)-β-D-葡萄糖呋喃糖苷]，通过相应的糖苷转化。研究发现，初花苷和绒毛苷的心变异构体仅由（R）-1-苯乙醇作为其苷元部分组成。
• Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase
  作者：Kei Shimoda、Hisashi Katsuragi

  DOI：10.1016/j.tetasy.2010.07.023

  日期：2010.8

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.
• 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。
• Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada

  DOI：10.1016/j.tetasy.2004.06.022

  日期：2004.8

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.