2-羟基苄基 beta-D-吡喃葡萄糖苷 | 7724-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基苄基 beta-D-吡喃葡萄糖苷
• 中文别名: 2-羟基苄基beta-D-吡喃葡萄糖苷
• 英文名称: isosalicin
• 英文别名: salicyl alcohol-7-O-β-D-glucopyranoside；(2-Hydroxy-benzyl)-β-D-glucopyranosid；2-Hydroxybenzyl beta-d-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2-hydroxyphenyl)methoxy]oxane-3,4,5-triol
• CAS: 7724-09-6
• 化学式: C₁₃H₁₈O₇
• 分子量: 286.282
• InChiKey: VBSPBYNZPRRGSB-UJPOAAIJSA-N

物化性质

• 熔点：
  67-69 °C
• 沸点：
  532.8±50.0 °C(Predicted)
• 密度：
  1.51

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  2-羟基苄基 beta-D-吡喃葡萄糖苷 在 β-glucosidase 作用下， 生成 a-无水葡萄糖酯 、 水杨醇
  参考文献：
  名称：

  Mitsuo, Naoki; Takeichi, Hiroshi; Satoh, Toshio, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 3, p. 1183 - 1187

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-hydroxy-benzyl)-(tetra-O-acetyl-β-D-glucopyranoside) 在 甲醇 、 sodium methylate 作用下， 生成 2-羟基苄基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Helferich; Liesen, Justus Liebigs Annalen der Chemie, 1950, vol. 570, p. 148,152

  摘要：

  DOI：

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。
• 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。
• 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.
• Helferich; Mueller von Blumencron, Chemische Berichte, 1953, vol. 86, p. 1058,1064
  作者：Helferich、Mueller von Blumencron

  DOI：——

  日期：——
• Enzyme-catalysed synthesis of alkyl β-D-Glucosides in organic media.
  作者：Gabin Vic、Daniel Thomas

  DOI：10.1016/s0040-4039(00)61314-x

  日期：1992.8

  The synthetic potential of Almond beta-D-Glucosidase for the synthesis of alkyl glucosides was studied. The regio and stereoselectivity of the synthesis were analysed for the reverse hydrolysis and the transglucosylation methods in tert-butanol and acetonitrile media.