tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside | 216876-40-3

• 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: tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-[tert-butyl(dimethyl)silyl]oxy-5-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)oxan-2-yl]methyl acetate
• CAS: 216876-40-3
• 化学式: C₂₄H₃₇NO₁₀Si
• 分子量: 527.644
• InChiKey: GGYBXRIGQYJEBO-ZFVCPDAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸 、 四丁基氟化铵 、 sodium methylate 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 8.0h， 生成 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k
• 作为产物：
  描述：

  2-deoxy-2-amino glucose 在 咪唑 、 乙酸肼 作用下， 反应 2.0h， 生成 tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k

文献信息

• Linear Synthesis of a Protected H-Type II Pentasaccharide Using Glycosyl Phosphate Building Blocks
  作者：Kerry Routenberg Love、Rodrigo B. Andrade、Peter H. Seeberger

  DOI：10.1021/jo015987h

  日期：2001.11.1

  a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally

  报道了利用糖基磷酸酯和糖基三氯乙酰亚氨酸酯结构单元线性合成完全受保护的H型II血型决定子五糖。设想了血型决定簇的自动固相合成，已证明糖基磷酸酯在逐步构建复杂的寡糖（例如H型II型抗原）中的效用。中央氨基葡萄糖结构单元的安装要求筛选各种氮保护基，以确保良好的氨基葡萄糖供体反应性和保护基的相容性。在存在其他羟基和胺保护基的情况下，区分末端半乳糖的C2的挑战促使我们引入2-（叠氮甲基）苯甲酰基作为碳水化合物合成的新型保护方式。检查了该基团与传统使用的保护基的相容性，以及其在糖基化中作为C2立体定向基团的用途。2-（叠氮甲基）苯甲酰基的应用以及对糖基供体的系统评价允许五糖的完成，并提供了预期普遍适用于血型决定簇的固相支持体合成的合成策略。
• NOVEL COMPOSITIONS AND THERAPEUTIC METHODS
  申请人：AyuVis Research LLC

  公开号：US20170281667A1

  公开（公告）日：2017-10-05

  The present invention is directed to novel products, variants, pharmaceutically acceptable salts and prodrugs thereof, and medical use of such compounds for the treatment and/or management of sepsis, septicemia, septic shock, ocular infection, ocular inflammation, ocular angiogenesis, rheumatoid arthritis (RA), atherosclerosis, inflammatory bowel diseases (IBD), asthma, chronic obstructive pulmonary disease, fever syndromes, cachexia, psoriasis, autoimmune diseases, cardiac diseases, retinoblastoma, cancer and/or any disorder associated with inflammation, immunomodulation and microbial infection.

  本发明涉及新产品、变体、药用可接受的盐和前药，以及这些化合物的医学用途，用于治疗和/或管理败血症、败血症、脓毒性休克、眼部感染、眼部炎症、眼部血管生成、类风湿性关节炎（RA）、动脉粥样硬化、炎症性肠病（IBD）、哮喘、慢性阻塞性肺病、发热综合征、消瘦症、牛皮癣、自身免疫疾病、心脏疾病、视网膜母细胞瘤、癌症和/或任何与炎症、免疫调节和微生物感染有关的疾病。