2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinyl-D-glucopyranose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinyl-D-glucopyranose
• 英文别名: Bz(-2)[Bn(-3)][levulinoyl(-4)][Bn(-6)]Glc；[(3R,4S,5R,6R)-2-hydroxy-5-(4-oxopentanoyloxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• 化学式: C₃₂H₃₄O₉
• 分子量: 562.617
• InChiKey: USAFPPXKCMTRHN-IQIYTOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinyl-D-glucopyranose 、 (2-(1-phenylvinyl)phenyl)methanol 在 2,2,2-三氟-N-苯基亚氨代乙酰氯 、 potassium carbonate 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到2-(1-phenylvinyl)benzyl 2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  基于邻-(1-苯基乙烯基)苄基糖苷的聚糖和核苷的一锅法合成

  摘要：

  聚糖和核苷的一锅法合成仍然很少见且具有挑战性。在此，我们报告了一种基于邻-(1-苯基乙烯基)苄基糖苷的聚糖和核苷合成的一锅糖基化策略，该策略具有几个优点，包括无糖苷配基转移、无离去物种的不良干扰、无难闻气味等。构建四种不同的糖苷键。

  DOI：

  10.1021/acs.orglett.1c02998
• 作为产物：
  描述：

  4-methylphenyl 2-O-benzoyl-3,6-O-dibenzyl-thio-β-D-glucopyranoside 在 哌啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-O-benzoyl-3,6-di-O-benzyl-4-O-levulinyl-D-glucopyranose
  参考文献：
  名称：

  Exploring and Exploiting the Reactivity of Glucuronic Acid Donors

  摘要：

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.

  DOI：

  10.1021/jo201586r

文献信息

• The total synthesis of rhynchosporosides <i>via</i> orthogonal one-pot glycosylation and stereoselective α-glycosylation strategies
  作者：Rui Yang、Xingchun Sun、Yunqin Zhang、Guozhi Xiao

  DOI：10.1039/d2ob01243j

  日期：——

  collective synthesis of rhynchosporosides causing scald diseases has been achieved, which features orthogonal one-pot glycosylation on the basis of PTFAI glycosylation, Yu glycosylation, and PVB glycosylation and merging reagent modulation and remote anchimeric assistance (RMRAA) α-glucosylation strategies. The issues inherent to the thioglycoside-based orthogonal one-pot glycosylation strategy, such as

  以PTFAI糖基化、Yu糖基化、PVB糖基化为基础的正交一锅法糖基化以及合并试剂调控和远程非嵌合辅助（RMRAA）α-糖基化策略，实现了高效、集体合成引起烫伤病的钩孢子苷。基于硫糖苷的正交一锅糖基化策略所固有的问题（例如糖苷配基转移）已被这种正交一锅糖基化策略排除，该策略可以简化聚糖的化学合成。
• Total Synthesis of Phellinus ribis Glycans with Immunostimulating Activities by an Orthogonal One-Pot Glycosylation Strategy
  作者：Jie Wan、Leilei Wang、Guozhi Xiao

  DOI：10.1055/a-1969-3992

  日期：2023.2

  achieved, which features orthogonal one-pot glycosylation strategy on the basis of N-phenyltrifluoroacetimidate (PTFAI) glycosylation, Yu glycosylation and ortho-(1-phenylvinyl)benzoate (PVB) glycosylation. The issues inherent to thioglycosides-based orthogonal one-pot glycosylation such as aglycone transfer have been precluded by this one-pot glycosylation strategy, which can streamline glycans chemical

  已经实现了具有强免疫刺激活性的桑黄聚糖的九糖重复单元和较短序列的全合成，其特点是基于 N-苯基三氟乙酰亚胺酯 (PTFAI) 糖基化、Yu 糖基化和邻位-(1-) 的正交一锅糖基化策略苯乙烯基）苯甲酸酯 (PVB) 糖基化。这种一锅糖基化策略排除了基于硫糖苷的正交一锅糖基化（如糖苷配基转移）所固有的问题，它可以简化聚糖的化学合成。
• 10.1021/jacs.4c05188
  作者：Chen, Zhiyuan、Xiao, Guozhi

  DOI：10.1021/jacs.4c05188

  日期：——

  challenging task in chemical synthesis. Here, we report the modular chemical synthesis of nona-decasaccharide motif from Ganoderma sinense polysaccharide GSPB70-S with diverse biological activities for the first time through one-pot stereoselective glycosylation strategy on the basis of glycosyl ortho-(1-phenyvinyl)benzoates, which not only sped up carbohydrates synthesis but also reduced chemical waste

  来自药用真菌灵芝的多糖代表了治疗多种疾病的重要辅助治疗剂，包括白细胞减少症和造血损伤。然而，从灵芝多糖中合成长的、支链的、复杂的碳水化合物链仍然是化学合成中的一项具有挑战性的任务。在此，我们首次报道了以糖基原-(1-苯乙烯基)苯甲酸酯为基础，通过一锅立体选择性糖基化策略，从灵芝多糖GSPB70-S中模块化化学合成了具有多种生物活性的九十糖基序。不仅加速了碳水化合物的合成，还减少了化学废物，并避免了基于硫代糖苷的一锅糖基化固有的糖苷配基转移问题。该合成路线还强调了以下关键步骤：（1）基于预激活的一锅糖基化，用于高度立体选择性构建多个1,2-顺式糖苷键，包括三个α- d -GlcN-（1→4）键和一个α- d -Gal-(1→4)键通过试剂N-甲基-N-苯基甲酰胺调节； (2)通过糖基N-苯基三氟乙酰亚胺酯、糖基邻炔基苯甲酸酯和糖基邻-(1-苯基乙烯基)苯甲酸酯的策略组合，在各种直链和支链聚糖片段中正交一锅组装1
• A One-Pot Synthesis of Glycans and Nucleosides Based on <i>ortho</i>-(1-Phenylvinyl)benzyl Glycosides
  作者：Rui Yang、Haiqing He、Zixi Chen、Yingying Huang、Guozhi Xiao

  DOI：10.1021/acs.orglett.1c02998

  日期：2021.11.5

  synthesis of both glycans and nucleosides remains rare and challenging. Herein, we report a one-pot glycosylation strategy for glycans and nucleosides synthesis based on ortho-(1-phenylvinyl)benzyl glycosides, which has several advantages, including no aglycon transfers, no undesired interference of departing species, no unpleasant odor, and up to the construction of four different glycosidic linkages

  聚糖和核苷的一锅法合成仍然很少见且具有挑战性。在此，我们报告了一种基于邻-(1-苯基乙烯基)苄基糖苷的聚糖和核苷合成的一锅糖基化策略，该策略具有几个优点，包括无糖苷配基转移、无离去物种的不良干扰、无难闻气味等。构建四种不同的糖苷键。
• Exploring and Exploiting the Reactivity of Glucuronic Acid Donors
  作者：Ana-Rae de Jong、Bas Hagen、Vincent van der Ark、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. Van der Marel

  DOI：10.1021/jo201586r

  日期：2012.1.6

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.