4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 141263-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: p-methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；p-methoxybenzyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；p-Methoxybenzyl 2,3,4,6-Tetra-O-Acetyl-beta-D-Galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(4-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate
• CAS: 141263-06-1
• 化学式: C₂₂H₂₈O₁₁
• 分子量: 468.458
• InChiKey: WSYXMFMRCHXIMF-CDJZJNNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 吡啶 、 三甲基氨基磺酸 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Regioselective sulfation of galactose derivatives through the stannylene procedure. New synthesis of the 3′-O-sulfated Lewisa trisaccharide

  摘要：

  Free or 6-protected beta-D-galactopyranosides afforded, in excellent yields, the 3'-O-sulfate as the only product through the stannylene procedure. This methodology was successfully applied to the synthesis of the 3'-O-sulfated Lewis(a) trisaccharide, an oligosaccharide reported as ligand of E- and L-selectins.

  DOI：

  10.1016/s0040-4039(00)78500-5
• 作为产物：
  描述：

  4-甲氧基苄醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  2,3,4,6- Te - O-烷基化D-葡萄糖和D-半乳糖的便捷合成

  摘要：

  描述了2,3,4,6-四-O-苄基化和烯丙基化的D-吡喃葡萄糖1和2以及相应的D-吡喃半乳糖3和4的方便的合成。D-葡萄糖衍生物1和2是从廉价的蔗糖中通过过烷基化和随后的酸水解获得的。在该反应序列中，产生烷基化的D-果糖呋喃糖基阳离子，该阳离子被不同的亲核试剂捕获，得到4-苄氧基亚甲基糠醛（8）和烷基化的D-果糖苷7、8和10。另一方面，2,3,4,6-四-O-苄基-D-半乳糖3通过用N-溴代琥珀酰亚胺水溶液氧化裂解乙基2,3,4,6-四-O-苄基-1-硫代-α，β-D-吡喃半乳糖苷（11）来合成。通过对甲氧基苄基β-D-葡糖苷制备2,3,4,6-四-O-烯丙基-D-吡喃葡萄糖苷（2）的替代途径吸引力较小。然而，被用于的2,3,4,6-四-合成此路线ö -allyl- d半乳糖（4）。

  DOI：

  10.1002/jlac.199719970124

文献信息

• [EN] HYDROLASE ENZYME SUBSTRATES AND USES THEREOF<br/>[FR] SUBSTRATS D'ENZYME HYDROLASE ET LEURS UTILISATIONS
  申请人：GEN ATOMICS

  公开号：WO2012099904A1

  公开（公告）日：2012-07-26

  The present invention provides novel methods for determining the presence or amount of a hydrolytic enzyme in a sample, based on novel substrates for the enzymes, and also provides compositions and methods that provide highly sensitive assay methods for such hydrolytic enzymes.

  本发明提供了一种新颖的方法，用于基于酶的新型底物确定样品中水解酶的存在或数量，并且提供了提供对这种水解酶进行高灵敏度测定的组合物和方法。
• Synthesis, Biological Activity of Salidroside and Its Analogues
  作者：Yibing Guo、Yahong Zhao、Cheng Zheng、Ying Meng、Yumin Yang

  DOI：10.1248/cpb.58.1627

  日期：——

  Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs–Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl)methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

  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。
• Synthesis of trisaccharide methyl glycosides related to fragments of the capsular polysaccharide of Streptococcus pneumoniae type 18C
  作者：Angusta M.P. van Steijn、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(00)90498-1

  日期：1992.3

  glucopyranosyl-beta-D-galactopyranoside 3-(sn-glycer-3-yl sodium phosphate) (4), which are trisaccharide methyl glycosides related to fragments of the capsular polysaccharide of Streptococcus pneumoniae type 18C ([----4)-beta-D- Glcp-(1----4)-[alpha-D-Glcp-(1----2)]-[Glycerol-(1-P----3)]-beta-D-Galp - (1----4)-alpha-D-Glcp-(1----3)-alpha-L-Rhap-(1----]n). Ethyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-be

  4-二-O-苄基-α-L-鼠李吡喃糖苷（6）。产物脱乙酰基，然后与2,4,6-三-O-乙酰基-3-O-烯丙基-α-D-吡喃并吡喃糖基三氯乙酰亚胺酸酯（18）缩合，得到苄基2,4-二-O-苄基-3 -O- [2,3,6-三-O-苄基-4-O-（2,4,6-三-O-乙酰基-3-O-烯丙基-β-D-吡喃半乳糖基）-α-D-吡喃葡萄糖基]-α-L-鼠李糖吡喃糖苷（19）。乙酰化19，然后进行甲基化，去甲酰化（---- 22），然后进一步脱保护，得到1.甲基2,4-二-O-苄基-3-O- [2,3,6-tri-O的缩合-苄基-4-O-（2,4,6-三-O-乙酰基-β-D-吡喃半乳糖基）-α-D-吡喃吡喃糖基]-α-L-鼠李糖吡喃糖苷（22）与1,2-二-O -苄基-sn-甘油3-（三乙基膦酸铵）（24），然后氧化和脱保护，得到2。2,3,4,6-四-O-苄基-1-硫代-β-乙基的缩合D-吡喃葡萄糖苷
• HYDROLASE ENZYME SUBSTRATES AND USES THEREOF
  申请人：Yuan Chong-Sheng

  公开号：US20120190013A1

  公开（公告）日：2012-07-26

  The present invention provides novel methods for determining the presence or amount of a hydrolytic enzyme in a sample, based on novel substrates for the enzymes, and also provides compositions and methods that provide highly sensitive assay methods for such hydrolytic enzymes.

  本发明提供了一种新的方法，用于基于新的酶底物确定样品中水解酶的存在或数量，并提供了组成物和方法，为这种水解酶提供高灵敏度的检测方法。
• Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate
  作者：Innaiah K. Polanki、Siva H. Kurma、Asish K. Bhattacharya

  DOI：10.1080/07328303.2015.1028585

  日期：2015.5.4

  Bi(NO3)(3), a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.