烯丙基2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-beta-D-苏-吡喃己糖苷 | 114853-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 烯丙基2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-beta-D-苏-吡喃己糖苷
• 中文别名: 烯丙基2-脱氧-2-邻苯二甲酰亚氨基-Β-D-吡喃葡萄糖苷
• 英文名称: allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: allyl 2-phthalimido-2-deoxy-β-D-glucopyranoside；Allyl 2-deoxy-2-phthalimido-b-D-glucopyranoside；2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-prop-2-enoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 114853-29-1
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: ZPZAUIIISMQKHG-CVXDVXMKSA-N

物化性质

• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  烯丙基2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-beta-D-苏-吡喃己糖苷 在 吡啶 、 咪唑 、 溶剂黄146 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 56.5h， 生成 allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  The development of new molecular tools containing a chemically synthesized carbohydrate ligand for the elucidation of carbohydrate roles via photoaffinity labeling: Carbohydrate–protein interactions are affected by the structures of the glycosidic bonds and the reducing-end sugar

  摘要：

  Photoaffinity labeling technology is a highly efficient method for cloning carbohydrate-binding proteins. When the carbohydrate probes are synthesized according to conventional methods, however, the reducing terminus of the sugar is opened to provide an acyclic structure. Our continued efforts to solve this problem led to the development of new molecular tools with an oligosaccharide structure that contains a phenyldiazirine group for the elucidation of carbohydrate-protein interactions. We investigated whether carbohydrate-lectin interactions are affected by differences in the glycosidic formation and synthesized three types of molecular tools containing Galp-GlcpNAc disaccharide ligands and a photoreactive group (1, 2, 3). Photoaffinity labeling validated the recognition of the new ligand by different glycosidic bonds. Photoaffinity labeling also demonstrated that both the reducing end sugar and non-reducing end sugar recognized the Erythrina cristagalli agglutinin.

  DOI：

  10.1016/j.bmc.2014.06.049
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 盐酸 、 氢溴酸 、 氰化汞 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 烯丙基2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-beta-D-苏-吡喃己糖苷
  参考文献：
  名称：

  Lamberth, Clemens; Nagy, Jon O.; Kasper, Cornelia, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 819 - 824

  摘要：

  DOI：

文献信息

• Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide
  作者：Ying Zhang、Fu-Long Zhao、Tao Luo、Zhichao Pei、Hai Dong

  DOI：10.1002/asia.201801486

  日期：2019.1.4

  was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2‐NPhth group and the C6‐OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth

  开发了Neu5Ac-α-2,3-LacNPhth三糖衍生物的简便方法。首先，研究了糖苷供体和葡萄糖NPhth二醇受体之间的区域/立体选择性糖基化。发现区域选择性不仅取决于葡糖胺受体的C2-NPhth基团和C6-OH保护基的空间位阻，还取决于糖苷供体的离去基团和保护基。在优化条件下，LacNPhth衍生物在高达92％的产率通过全乙酰-α-D-吡喃半乳糖三氯之间的区域选择性/立体选择性糖基化合成p -甲氧基苯基6- ö -叔-butyldiphenylsilyl -2-脱氧-2-苯二甲酰亚-β- d-吡喃葡萄糖苷，避免形成糖基化原酸酯和异头糖苷配基。然后，将LacNPhth衍生物脱酰基，然后通过TBDPS保护在伯位置上，以形成LacNPhth多元醇受体。最后，通过LacNPhth多元醇受体与亚磷酸唾液酸基酯供体之间的区域/立体选择性糖基化反应，以48％的产率合成了Neu5Ac-α-2,3-La
• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。
• Efficient Acetylation of Carbohydrates Promoted by Imidazole
  作者：Pallavi Tiwari、Rishi Kumar、Prakas R. Maulik、Anup Kumar Misra

  DOI：10.1002/ejoc.200500555

  日期：2005.10

  An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  据报道，由咪唑促进的碳水化合物衍生物和未受保护的还原糖的有效过-O-乙酰化。该反应条件已成功用于乙酰化含有酸敏感官能团的碳水化合物衍生物。在大多数情况下，获得的产率非常好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• [EN] SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCOCCUS VACCINE<br/>[FR] OLIGOSACCHARIDES SYNTHÉTIQUES DESTINÉS À UN VACCIN CONTRE UN STAPHYLOCOQUE
  申请人：ANCORA PHARMACEUTICALS INC

  公开号：WO2012145626A1

  公开（公告）日：2012-10-26

  The present invention synthetic oligo-β-(1→6)-glucosamine structures and a methodology which essentially allows for the synthesis of any oligo-β-(1→6)-glucosamine species having a definite number of monosaccharide units, including a set pattern of acetylated and non- acetylated residues. The invention further provides antibodies to these synthetic oligo-β-(1→6)-glucosamines as well as compositions thereof and methods for treating and preventing infections caused by bacteria expressing poly-β-(1→6)-glucosamines, such as Staphylococcus aureus.

  本发明提供了合成寡聚β-(1→6)-葡聚糖结构以及一种方法，基本上允许合成具有明确单糖单位数量的任何寡聚β-(1→6)-葡聚糖物种，包括一组乙酰化和非乙酰化残基的设定模式。该发明还提供了针对这些合成寡聚β-(1→6)-葡聚糖的抗体，以及其组合物和用于治疗和预防由表达多聚β-(1→6)-葡聚糖的细菌引起的感染的方法，例如金黄色葡萄球菌。