1-O-benzyl-N-acetyl-4,6-O-benzylidene-D-glucosamine | 101223-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-O-benzyl-N-acetyl-4,6-O-benzylidene-D-glucosamine
• 英文别名: benzyl 2-acetamido-2-deoxy-4,6-O-benzylidene-D-glucopyranoside；benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-D-glucopyranoside；Benzyl-2-acetamido-4,6-O-benzyliden-2-deoxy-D-glucopyranosid；Benzyl-2-acetamido-4,6-O-benzyliden-D-glucopyranosid；N-[(4aR,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 101223-84-1；3554-91-4；13343-61-8；13343-63-0；19374-64-2；27539-62-4；38191-73-0；78246-81-8；78247-23-1；81655-20-1；117182-56-6；134308-75-1
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: NXGXFAKJUWEFEC-ZHEILYIOSA-N

物化性质

• 沸点：
  650.6±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-N-acetyl-4,6-O-benzylidene-D-glucosamine 在 N,N'-羰基二咪唑 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 N-[(4aR,6S,7R,8R,8aR)-8-(12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yloxy)-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]pyridine-2-carboxamide
  参考文献：
  名称：

  Synthesis of novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions

  摘要：

  A new type of phosphate-pyridine (P, N) ligand derived from D-glucosamine and BINOL was synthesized and successfully applied in Cu-catalyzed enantioselective conjugate addition of diethylzinc to chalcones for the first time, high yields and enantioselectivities were obtained when the ligand 10a which contains (S)-BINOL was used. The results also showed that the configuration of BINOL at the ligand backbone had remarkable effects on the activities and enantioselectivities. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2011.09.021
• 作为产物：
  描述：

  benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 在 氯化锌 作用下， 以 P₂O₅ 、 乙醚 、 乙醇 、 水 、 苯甲醛 为溶剂， 以62.6%的产率得到1-O-benzyl-N-acetyl-4,6-O-benzylidene-D-glucosamine
  参考文献：
  名称：

  Fluorinated glucosamine analogs useful for modulating post-translational glycosylations on cells

  摘要：

  本发明提供了抑制细胞迁移的组合物和方法，例如淋巴细胞和炎症。该发明还提供了一种改进的制备氟化N-乙酰葡萄糖胺的方法。

  公开号：

  US20030148997A1

文献信息

• NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF
  申请人：BHARAT BIOTECH INTERNATIONAL LIMITED

  公开号：US20180360957A1

  公开（公告）日：2018-12-20

  The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof; wherein R 1 and R 2 both are hydrogen; or R 1 is hydrogen and R 2 is alkyl or aryl; or R 1 is alkyl or aryl and R 2 is hydrogen; or R 1 and R 2 both are alkyl or aryl (same or different groups); wherein alkyl group constitute C1-C6 alkyl or higher (both linear and branched) with or without heteroatoms; and aryl group constitute phenyl, substituted phenyl, heteraryl, arylalkyl and polynuclear aromatics. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

  该发明涉及结构式-VIII的新型Muramyl二肽（MDP）衍生物化合物，以及用于合成的过程、合成中使用的中间体和其用途；其中R1和R2均为氢；或者R1为氢且R2为烷基或芳基；或者R1为烷基或芳基且R2为氢；或者R1和R2均为烷基或芳基（相同或不同基团）；其中烷基基团包括C1-C6烷基或更高碳数（线性和支链）且可能含有杂原子；芳基基团包括苯基、取代苯基、杂芳基、芳基烷基和多核芳香族。这些化合物具有出色的药理特性，特别是作为疫苗配方中的辅助免疫调节剂的用途。这些化合物在疫苗中作为辅助剂特别有用。
• [EN] NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF<br/>[FR] NOUVEAU COMPOSÉ DÉRIVÉ DE MURAMYLE, SYNTHÈSE ET UTILISATIONS ASSOCIÉES
  申请人：BHARAT BIOTECH INT LTD

  公开号：WO2017098529A1

  公开（公告）日：2017-06-15

  The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

  这项发明涉及结构式-VIII的新型Muramyl Dipeptide（MDP）衍生物化合物，以及用于合成的过程、合成中使用的中间体和其用途。其中，R = 烷基（线性和支链）、芳基、取代芳基、烷氧基烷基。其中，R可以是线性和支链烷基、芳基、取代芳基和烷氧基烷基。这些化合物具有出色的药理特性，特别是作为疫苗配方中的辅助免疫调节特性。这些化合物在疫苗中特别有用作为辅助剂。
• Novel Phosphoramidate Prodrugs of <i>N-</i>Acetyl-(<scp>d</scp>)-Glucosamine with Antidegenerative Activity on Bovine and Human Cartilage Explants
  作者：Michaela Serpi、Rita Bibbo、Stephanie Rat、Helen Roberts、Claire Hughes、Bruce Caterson、María José Alcaraz、Anna Torrent Gibert、Carlos Raul Alaez Verson、Christopher McGuigan

  DOI：10.1021/jm300074y

  日期：2012.5.24

  4-methoxy phenyl group and different amino acid esters on the phosphate moiety. Among the compounds, the (l)-proline amino acid-containing prodrugs proved to be the most active of the series, more effective than the prior O-6 compounds, and well processed in chondrocytes in vitro. Data on human cartilage support the notion that these novel O-3 and O-4 regioisomers may represent novel promising leads

  （d）-氨基葡萄糖和其他营养补充剂已作为骨关节炎（OA）（一种慢性和退化性关节病）的安全替代疗法出现。在我们的前述纸，一系列新O-6磷酸ñ -乙酰基（d）旨在改善的口服生物利用度的前药-葡糖胺ñ -乙酰基- （d） -葡糖胺作为其生物活性的推定磷酸形式显示出具有更大的软骨保护与母体药物相比具有体外活性。为了扩展SAR研究，这项工作着眼于N-乙酰-（d的O-3和O-4磷酸盐前药）-在氨基磷酸酯部分带有4-甲氧基苯基和不同的氨基酸酯的氨基葡萄糖。在这些化合物中，含（l）-脯氨酸氨基酸的前药被证明是该系列中最活跃的，比以前的O-6化合物更有效，并且在体外软骨细胞中加工良好。关于人类软骨的数据支持以下观念：这些新型O-3和O-4区域异构体可能代表了骨关节炎药物发现的新的有前途的线索。
• Phosphoramidates of monosaccharides
  申请人：Bioiberica, S.A.

  公开号：EP2471802A1

  公开（公告）日：2012-07-04

  The present invention relates novel phosphoramidates of monosaccharides of formula (I), wherein R1 is a monosaccharide group selected from A and B; R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and X are as defined herein. Preferably X is -O-. The present invention also provides processes for the production of compounds of formula (I), pharmaceutical compositions comprising these compounds, as well as to the use thereof in medical therapy, preferably in the treatment of osteoarthritis. wherein: R1 is selected from A and B,

  本发明涉及公式(I)的单糖磷酰胺的新型磷酸酰胺，其中R1是从A和B中选择的单糖基团；R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16和X如本文所定义。优选X为-O-。本发明还提供了制备公式(I)化合物的方法，包括含有这些化合物的药物组合物，以及在医学治疗中的使用，优选用于骨关节炎的治疗。其中：R1从A和B中选择。
• Optimization of UDP-N-acetylmuramic acid synthesis
  作者：Humljan, Jan、Starcevic、Car、Stefanic Anderluh、Kocjan、Jenko、Urleb

  DOI：10.1691/ph.2008.7675

  日期：——

  UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-MurNAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.

  UDP-N-乙酰肟酸（UDP-MurNAc）是MurC的底物，MurC是细菌肽聚糖生物合成细胞内途径中的重要酶。已经发布了多种制备UDP-MurNAc的方法，但这些合成准备显示出许多问题步骤。进行了一项优化研究，重点关注肽聚糖磷酸盐和UMP-吗啉酸酯的耦合，最终实现了一种合成程序，使得在多克朗规模上进行稳健且易于复制的生产成为可能。