甲基2-乙酰氨基-2-脱氧-3,6-二-O-苄基-beta-D-吡喃葡萄糖苷 | 144685-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基2-乙酰氨基-2-脱氧-3,6-二-O-苄基-beta-D-吡喃葡萄糖苷
• 英文名称: methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 3,6-dibenzyl-beta-N-acetylglucosamine；N-[(2R,3R,4R,5S,6R)-5-Hydroxy-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 144685-11-0
• 化学式: C₂₃H₂₉NO₆
• 分子量: 415.486
• InChiKey: POXMMSHWVBSCKK-GNJRFXKQSA-N

物化性质

• 溶解度：
  可溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  甲基2-乙酰氨基-2-脱氧-3,6-二-O-苄基-beta-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 四丁基氟化铵 、 氢气 作用下， 以 乙腈 为溶剂， 反应 216.0h， 生成 methyl 2-acetamido-2,4-dideoxy-4-fluoro-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-galactose and their effects on cellular glycosaminoglycan biosynthesis

  摘要：

  4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00049-5
• 作为产物：
  描述：

  methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以66%的产率得到甲基2-乙酰氨基-2-脱氧-3,6-二-O-苄基-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Cromer, Remy; Spohr, Ulrike; Khare, Deveshwari P., Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1511 - 1530

  摘要：

  DOI：

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• [EN] SULFATED OLIGOSACCHARIDES FOR USE IN TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] OLIGOSACCHARIDES SULFATÉS À UTILISER DANS LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：KING S COLLEGE LONDON

  公开号：WO2012160337A1

  公开（公告）日：2012-11-29

  Compounds which interact with HlsTONES Compounds of Formula I : • 4"'-Sulfo-Fucose [alpha]1-3 (4"-sulfo)-Fucose [alpha]1-3 (4'-Sulfo-Fu- cose [alpha]1-4-Glucuronic acid [beta]1-0-Methyl or • 4" "-Sulfo-Fucose [alpha]1-3 (4"-sulfo)-Fucose [alpha]1-3 (4"-sulfo)- Fucose [alpha]1-3 (4'-Sulfo-Fucose [alpha]1-4-Glucuronic acid [be ta]1-0-Methyl. wherein X is sulfate (-SO3H) or phosphate (-PO3H); Su is sulfate and sulfation is most likely at the arrowed positions. The compounds above are useful in the inhibition of histones, in particular histone H1. The compounds can be used in medicine and particularly in the prevention and/or treatment of a wide variety of neurodegenerative diseases, including Alzheimer's disease and Parkinson's disease.

  与HlsTONES Formula I 化合物相互作用的化合物包括：• 4"'-糖基硫酸酯 [alpha]1-3 (4"-糖基硫酸酯) [alpha]1-3 (4'-糖基硫酸酯 [alpha]1-4-葡萄糖醛酸 [beta]1-0-甲基或• 4" "-糖基硫酸酯 [alpha]1-3 (4"-糖基硫酸酯) [alpha]1-3 (4"-糖基硫酸酯)- 糖基 [alpha]1-3 (4'-糖基硫酸酯 [alpha]1-4-葡萄糖醛酸 [be ta]1-0-甲基。其中 X 是硫酸酯基 (-SO3H) 或磷酸酯基 (-PO3H)；Su 是硫酸酯基，磺酸化最有可能发生在箭头所指位置。上述化合物对于抑制组蛋白，特别是组蛋白 H1，具有用处。这些化合物可用于医药领域，尤其是用于预防和/或治疗多种神经退行性疾病，包括阿尔茨海默病和帕金森病。
• Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei
  作者：Simon Krauter、Christina Schäffer、Paul Kosma

  DOI：10.24820/ark.5550190.p011.358

  日期：——

  A disaccharide implicated in anchoring of bacterial Surface-layer proteins to secondary cell wall glycopolymers has been prepared by glycosylation of a protected N-acetyl glucosamine acceptor with a glucopyranosyl donor to generate the β-(14)-linkage. Subsequent inversion of the configuration and azide introduction at position 2 with triflic anhydride, however, led to formation of a tetrazole derivative

  通过将受保护的 N-乙酰氨基葡萄糖受体与吡喃葡萄糖基供体进行糖基化以产生 β-(1→4)-键，已经制备了一种与细菌表面层蛋白锚定到次生细胞壁糖聚合物有关的二糖。然而，随后用三氟甲磺酸酐反转构型和在 2 位引入叠氮化物，导致形成四唑衍生物。或者，通过叠氮化钠、还原和 N-乙酰化置换 2O-甲磺酸盐能够转化为远端 N-乙酰基-β-甘露糖胺残基。后一个单元的丙酮酸化和全局脱保护提供了来自类芽孢杆菌的双糖重复单元作为晶体学和结合研究的配体。
• 10.1002/(sici)1099-0690(199806)1998:6<1099::aid-ejoc1099<3.0.co;2-r
  作者：Ogawa, Seiichiro、Hirai, Keisuke、Odagiri, Takashi、Matsunaga, Naoki、Yamazaki, Tetsuya、Nakajima, Akihiro

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1099::aid-ejoc1099<3.0.co;2-r

  日期：——
• Synthesis and biological evaluation of a radiolabeled analog of methyl 2-acetamido-2,4-dideoxy-β-d-xylo-hexopyranoside directed towards influencing cellular glycosaminoglycan biosynthesis
  作者：Ali Berkin、Walter A Szarek、Robert Kisilevsky

  DOI：10.1016/s0008-6215(01)00285-3

  日期：2002.1

  Two methods are presented for the synthesis or methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside. The first method employs the Barton-McCombie deoxygenation methodology, and the second method utilizes an oxidation-beta-elimination methodology that allows for the incorporation of hydrogen isotopes into the title compound. Hence, methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (4) and methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside-6-t (14) were synthesized and evaluated for their ability to inhibit hepatocyte, cell-surface glycosaminoglycan biosynthesis and to incorporate a [H-3] radiolabel into isolated glycosaminoglycans, respectively. Compound 4, at a concentration of 1.0 mM, demonstrated a reduction of D-[H-3]glucosamine and [S-35]sulfate incorporation into isolated glycosaminoglycans by 69 and 59%, of the control cultures, respectively. At 10 and 20 mM, 4 demonstrated a maximum inhibition of incorporation of both radiolabels to approximately 10% of the control cultures. Compound 14 demonstrated a maximum incorporation of a [H-3] radiolabel into isolated cell-surface glycosaminoglycans at 10 and 20 mM. The mechanism of inhibition of glycosaminoglycan biosynthesis is due, in part, to the incorporation of a 4-deoxy moiety into glycosaminoglycan chains resulting in premature chain termination. (C) 2002 Elsevier Science Ltd. All rights reserved.