2-苯基乙基 beta-D-吡喃葡萄糖苷 | 18997-54-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯基乙基 beta-D-吡喃葡萄糖苷
• 中文别名: 2-苯基乙基beta-D-吡喃葡萄糖苷；苯基乙基 BETA-D-吡喃葡萄糖苷
• 英文名称: 2-phenylethyl-β-D-glucopyranoside
• 英文别名: phenethyl β-D-glucopyranoside；2-phenylethyl-O-β-D-glucopyranoside；2-phenylethyl β-D-glucoside；2-phenylethyl β-glucopyranoside；phenethyl O-β-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-phenethoxytetrahydro-2H-pyran-3,4,5-triol；phenylethyl O-β-D-glucopyranoside；2-phenylethyl beta-D-glucopyranoside；Phenylethyl beta-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol
• CAS: 18997-54-1
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: MLRIJUWUQTVDQE-RKQHYHRCSA-N

物化性质

• 熔点：
  115 - 117°C
• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 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

安全信息

• WGK Germany：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside	——	C22H28O10	452.458
  纤维素二糖	Cellobiose	16462-44-5	C12H22O11	342.3
  ——	2-phenylethyl tetra-O-benzoyl-β-D-glucopyranoside	1038587-84-6	C42H36O10	700.742
  a-无水葡萄糖酯	alpha-D-glucopyranose	492-62-6	C6H12O6	180.158
  可得然胶	β-D-glucose	492-61-5	C6H12O6	180.158
  D-葡萄糖	D-glu	2280-44-6	C6H12O6	180.158
  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯	D-glucose pentaacetate	83-87-4	C16H22O11	390.344
  β-D-葡萄糖五乙酸酯	β-D-glucose pentaacetate	604-69-3	C16H22O11	390.344
  α-D(+)-五乙酰葡萄糖	α-D-glucopyranose peracetylate	604-68-2	C16H22O11	390.344
  ——	2,3,4,5-tetra-O-acetyl-D-glucopyranose	——	C14H20O10	348.307
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (2R,3R,4S,5S,6R)-2-(2-苯基乙氧基)-6-[[(2S,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基甲基]四氢吡喃-3,4,5-三醇	2-phenylethyl β-primeveroside	129932-48-5	C19H28O10	416.425
  ——	2-phenylethyl d-rutinoside	88510-08-1	C20H30O10	430.452
  ——	phenethanol-β-vicianoside	125572-77-2	C19H28O10	416.425
  ——	2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside	——	C22H28O10	452.458
  ——	2-phenylethyl hexa-O-acetyl β-rutinoside	88510-13-8	C32H42O16	682.676
  ——	2-phenylethanol glucuronide	18997-55-2	C14H18O7	298.293
  ——	phenethyl 6-O-trityl-β-D-glucopyranoside	860648-07-3	C33H34O6	526.629
  a-无水葡萄糖酯	alpha-D-glucopyranose	492-62-6	C6H12O6	180.158
  D-葡萄糖	D-glu	2280-44-6	C6H12O6	180.158

反应信息

• 作为反应物：
  描述：

  2-苯基乙基 beta-D-吡喃葡萄糖苷 在 palladium hydroxide - carbon 4-二甲氨基吡啶 、 氢气 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Naturally Occurring Phenethyl (1→6)-β-D-Glucopyranosides

  摘要：

  DOI：

  10.3987/com-05-10383
• 作为产物：
  描述：

  2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以92%的产率得到2-苯基乙基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis, Biological Activity of Salidroside and Its Analogues

  摘要：

  红景天苷是从传统中草药红景天中分离得到的一种苯丙素苷类化合物，具有广泛的药理活性。本文通过Koenigs-Knorr方法合成了约18种新颖的红景天苷类似物，并利用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴盐（MTT）法评估了这些化合物对PC12细胞的影响。这些新颖化合物在苯环上的取代基或糖基供体方面有所不同。根据数据，苯环3和5位带有甲氧基的(3,5-二甲氧基苯基)甲基β-D-葡萄吡喃糖苷和(3,5-二甲氧基苯基)甲基β-D-半乳吡喃糖苷在浓度分别为300 μmol/L和60 μmol/L时显示出最高的细胞生存力。

  DOI：

  10.1248/cpb.58.1627

文献信息

• 2-<i>O</i>-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation
  作者：Julia Weber、Dennis Svatunek、Simon Krauter、Gregor Tegl、Christian Hametner、Paul Kosma、Hannes Mikula

  DOI：10.1039/c9cc07194f

  日期：——

  idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O-2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1,2-trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.

  通过恢复一个古老的想法，我们证明了烷氧基羰基可用于糖基化反应，以通过在O -2处的碳酸酯部分的参与来实现完全的立体控制。制备了各种苄氧羰基保护的糖基供体，并将其用于对碱不稳定的化合物进行有效的1，2-反式糖基化和糖基酯的合成。
• Expression and Biochemical Characterization of β-Primeverosidase and Application of β-Primeverosylamidine to Affinity Purification
  作者：Hiromichi SAINO、Masaharu MIZUTANI、Jun HIRATAKE、Kanzo SAKATA

  DOI：10.1271/bbb.70447

  日期：2008.2.23

  β-Primeverosidase (PD) is a family 1 glycosidase catalyzing the hydrolysis of β-primeverosides (6-O-β-d-xylopyranosyl-β-d-glucopyranosides) to release a disaccharide primeverose. To investigate how PD recognizes the disaccharide moiety of β-primeverosides, the recombinant PD was expressed by a baculovirus-insect cell system. The recombinant PD was secreted from High Five cells and was properly modified with N-glycosylation and correct cleavage at the N-terminal signal peptide. The recombinant PD exhibited high substrate specificity to β-primeverosides in terms of the glycone moiety, consistently with the substrate specificity of native PD from Camellia sinensis. Next, β-glycosylamidines were synthesized as substrate analog inhibitors. β-Primeverosylamidine strongly inhibited PD activity, but β-glucosylamidine did not. Hence β-primeverosylamidine is an ideal chemical tool for probing disaccharide recognition in the active site of PD. An affinity adsorbent for PD was prepared using β-primeverosylamidine as a ligand. Affinity chromatography gave large amounts of PD with high purity, permitting crystallographic study.

  β-Primeverosidase（PD）是一种家族1糖苷酶，催化β-早春花苷（6-O-β-d-木糖吡喃糖基-β-d-葡萄吡喃糖苷）水解，释放出早春花二糖。为了研究PD如何识别β-早春花苷的二糖部分，我们通过杆状病毒-昆虫细胞系统表达了重组PD。重组PD从High Five细胞中分泌出来，并进行了N-糖基化修饰和N端信号肽的正确切割。重组PD对β-早春花苷的糖苷部分表现出高度的底物特异性，与茶树中天然PD的底物特异性一致。接下来，合成了β-糖苷酰胺作为底物类似物抑制剂。β-早春花苷酰胺强烈抑制PD活性，而β-葡萄糖苷酰胺没有抑制作用。因此，β-早春花苷酰胺是一个理想的化学工具，用于探测PD活性位点中二糖的识别。使用β-早春花苷酰胺作为配体制备了PD的亲和吸附剂。亲和层析获得了高纯度的大量PD，允许进行晶体学研究。
• Substrate Specificity of β-Primeverosidase, A Key Enzyme in Aroma Formation during Oolong Tea and Black Tea Manufacturing
  作者：Seung-Jin MA、Masaharu MIZUTANI、Jun HIRATAKE、Kentaro HAYASHI、Kensuke YAGI、Naoharu WATANABE、Kanzo SAKATA

  DOI：10.1271/bbb.65.2719

  日期：2001.1

  monoglycoside of 2-phenylethanol to investigate the substrate specificity of the purified beta-primeverosidase from fresh leaves of a tea cultivar (Camellia sinensis var. sinensis cv. Yabukita) in comparison with the apparent substrate specificity of the crude enzyme extract from tea leaves. The crude enzyme extract mainly showed beta-primeverosidase activity, although monoglycosidases activity was present

  我们合成了9种二糖苷和2-苯基乙醇单糖苷，以研究茶树种（Camellia sinensis var。sinensis cv。Yabukita）鲜叶中纯化的β-primeverosidase的底物特异性，并比较其表面底物特异性。茶叶中的粗酶提取物。粗酶提取物主要表现出β-primeverosidase活性，尽管在一定程度上存在单糖苷酶活性。纯化的β-primeverosidase对糖蛋白部分显示非常狭窄的底物特异性，尤其是对β-primeverosyl（6-O-β-D-吡喃吡喃糖基-β-D-葡萄糖基吡喃糖基）部分的特异性。这些酶会水解天然存在的二糖苷，例如β-primeveroside，β-vicianoside，β-acuminoside，β-龙胆苷和6-O-α-L-阿拉伯呋喃糖基-β-D-吡喃葡萄糖苷，但无法水解合成的非天然二糖苷。纯化的酶对2-苯乙基β-D-吡喃葡萄糖苷没有活性。该酶将
• Concise synthesis of glyconoamidines as affinity ligands for the purification of β-glucosidase involved in control of some biological events including plant leaf movement
  作者：Eisuke Kato、Tadahiro Kumagai、Minoru Ueda

  DOI：10.1016/j.tetlet.2005.05.060

  日期：2005.7

  biochemical studies and would be useful as an affinity ligand for purification of glycosidase. However, its use for the specific inhibition of glucosidase which is highly specific to a glycoside with voluntary aglycon is seriously restricted because no universal method for the synthesis of N-alkylated glyconoamidine has been reported. Here, we report a concise synthesis of N-alkylated Ganem’s glyconoamidine

  糖苷酶通过生物有趣的过程参与某些内源性生物活性物质的失活或储存。例如，通过生物钟通过β-葡萄糖苷酶活性的调节来控制夜蛾叶片的运动。Ganem的糖氨（1）在生化研究中用作葡糖苷酶的微摩尔抑制剂，可用作糖苷酶纯化的亲和配体。但是，由于没有报道用于合成N-烷基化的糖氨am的通用方法，因此严重限制了其对对具有自愿糖苷配基的糖苷高度特异性的葡糖苷酶的特异性抑制的用途。在这里，我们报告N的简明综合使用未保护的糖衍生物，用自愿糖苷酸将Ganem's糖氨am酸烷基化。
• Compounds for a controlled release of active molecules
  申请人：FIRMENICH SA

  公开号：US09550960B2

  公开（公告）日：2017-01-24

  The present invention relates to the field of perfumery. More particularly, it concerns compounds comprising at least one β-glucuronide moiety capable of liberating a perfuming alcohol. The present invention concerns also the use of said compounds in perfumery as well as the perfuming compositions or perfumed articles, in particular deodorants or antiperspirants comprising the invention's compounds.

  本发明涉及香水领域。更具体地，涉及包含至少一个能释放香精醇的β-葡萄糖醛酸酯基团的化合物。本发明还涉及在香水中使用所述化合物，以及包含该发明化合物的香水配方或香水制品，特别是包含该发明化合物的除臭剂或止汗剂。