methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside | 190515-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]a-Glc1Me；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxy-2-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 190515-39-0
• 化学式: C₆₂H₆₀O₁₄
• 分子量: 1029.15
• InChiKey: RGZPHINDFHDVMO-UDZCAKAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  n-propyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 triphenyl bismuth ditriflate 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  铋（V）介导的硫糖苷活化

  摘要：

  开发了一种简单的利用铋（V）化合物的方法来激活硫丙基丙基糖苷以偶联到各种受体上。在不使用其他添加剂/助促进剂的情况下获得了良好至极好的收率。该方法不需要低温，适用于多种碳水化合物，并且可以耐受包括烯烃在内的不同官能团。

  DOI：

  10.1002/anie.201304099

文献信息

• Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates
  作者：Jianbo Zhang、Guosheng Sun、Yue Wu、Anqi Liu、Saifeng Qiu、Wan Zhang、Zhongfu Wang

  DOI：10.1055/s-0036-1591525

  日期：2018.3

  Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective

  已经描述了使用 FeCl3 作为糖基供体的糖苷。在最佳反应条件下，发现三种炔丙基糖苷与类固醇和糖衍生的糖基受体反应，以良好至极好的收率（66-91%）提供相应的二糖和糖缀合物。同时，该方法还可实现双糖的一锅法合成，是一种高效、经济、绿色的糖基化方法。
• OFox imidates as versatile glycosyl donors for chemical glycosylation
  作者：Swati S. Nigudkar、Tinghua Wang、Salvatore G. Pistorio、Jagodige P. Yasomanee、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1039/c6ob02230h

  日期：——

  mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical

  以前，我们交流了3,3-二氟己二酮（HOFox）介导的糖基化作用，其中发现3,3-二氟-3 H-吲哚-2-基（OFox）酰亚胺化是关键中间体。无论是在原位由相应的糖基溴化物和亚胺酸酯OFox活化合成可以在再生的方式进行。在这里，我们扩展了这项研究，主要侧重于各种OFox酰亚胺的合成及其作为化学1,2-顺式和1,2-反式糖基化的糖基供体的研究。
• Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides
  作者：Srinivasa Rao Vidadala、Srinivas Hotha

  DOI：10.1039/b822526e

  日期：——

  Stable methyl glycosides are identified as glycosyl donors in the presence of AuBr(3) in acetonitrile; a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols are examined successfully for the glycosylation reaction and methyl glycosides of di- and tri- saccharides are converted to corresponding tri- and tetra-saccharides exploiting salient features of our novel activation

  在乙腈中存在AuBr（3）的情况下，稳定的甲基糖苷被鉴定为糖基供体；利用我们新颖的激活方案的显着特征，成功地检测了一组包含脂肪族，脂环族，甾族和糖醇的糖苷配基的糖基化反应，并将二糖和三糖的甲基糖苷转化为相应的三糖和四糖。
• AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature
  作者：Ashokkumar Palanivel、Ande Chennaiah、Sateesh Dubbu、Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1016/j.carres.2016.11.012

  日期：2017.1

  glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20-60 min)

  已经描述了使用AuCl3 / AgOTf试剂系统将亚砜活化为糖基供体。在最佳反应条件下，发现武装和解除武装的糖基亚砜供体都与一定范围的伯，仲和叔醇受体和糖衍生的糖基受体反应，以中等到良好的产率提供了可预测的选择性的相应糖苷。反应快速（20-60分钟），在室温下容易进行，并且反应条件可耐受酸敏感性基团。
• Use of the methylsulfenyl cation as an activator for glycosylation reactions with alkyl (aryl) l-thioglycopyranosides: synthesis of methyl O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→ 2)-α-d-glucopyranoside, a derivative of the core trisaccharide of E. coli K12
  作者：Falguni Dasgupta、Per J. Garegg

  DOI：10.1016/0008-6215(90)84082-6

  日期：1990.7

  Methylsulfenyl bromide (MSB) and methylsulfenyl trifluoromethanesulfonate (MST) have been used to prepare 1,2-cis-linked disaccharides. Ethyl (phenyl) 1-thio-beta-D-gluco- and galacto-pyranosides having non-participating (benzyloxy) protecting groups were used as the donors. The alpha beta-ratio of the products depended on the promoter and conditions of reaction. Intimate ion-pairs, formed initially

  甲基亚磺酰基溴（MSB）和甲基亚磺酰基三氟甲磺酸盐（MST）已用于制备1,2-顺式连接的二糖。具有非参与式（苄氧基）保护基的乙基（苯基）1-硫-β-D-葡萄糖基和半乳糖吡喃糖苷用作供体。产物的α-β比率取决于启动子和反应条件。最初形成的亲密离子对可能对糖基化的空间结果负责。因此，用乙基2,3,4,6-四-O-苄基-α-D-甘露吡喃糖苷作为供体，使用MSB作为活化剂可以生产适量的β-连接的二糖。描述了含有1，2-顺式和1，2-反式连接的标题三糖苷的合成。