1,2-Di-O-acetyl-3,5-di-O-benzyl-α-D-xylofuranose | 134953-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-Di-O-acetyl-3,5-di-O-benzyl-α-D-xylofuranose
• 英文别名: [(2R,3R,4S,5R)-2-acetyloxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] acetate
• CAS: 134953-48-3
• 化学式: C₂₃H₂₆O₇
• 分子量: 414.455
• InChiKey: QQEKCYXHFJIXJS-ACESQOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 IRN 77 (H+) 、 sodium hydride 作用下， 反应 42.75h， 生成 1,2-Di-O-acetyl-3,5-di-O-benzyl-α-D-xylofuranose
  参考文献：
  名称：

  Benhaddou, R.; Czernecki, S.; Valery, J. M., Bulletin de la Societe Chimique de France, 1991, # 1, p. 108 - 111

  摘要：

  DOI：

文献信息

• Synthesis of Purine Nucleosides from<scp>D</scp>-Glucuronic Acid Derivatives and Evaluation of Their Cholinesterase-Inhibitory Activities
  作者：Nuno M. Xavier、Stefan Schwarz、Pedro D. Vaz、René Csuk、Amélia P. Rauter

  DOI：10.1002/ejoc.201301913

  日期：2014.5

  Glucuronolactones were used as precursors for N9 and N7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine

  葡萄糖醛酸内酯被用作 N9 和 N7 嘌呤核苷的前体，其结构中含有葡萄糖醛酸衍生物。乙酰化 N-苄基葡糖醛酸酰胺和吡喃葡萄糖醛酸酰胺是从呋喃葡萄糖醛酸-6,3-内酯通过几个步骤合成的。在三甲基甲硅烷基三氟甲磺酸酯的存在下，通过与甲硅烷基化的 2-乙酰氨基-6-氯嘌呤进行 N-糖基化，将它们转化为相应的呋喃糖基和吡喃糖基糖醛酰胺基核苷。三乙酰化双环内酯本身与核碱基偶联，得到双环 N9,N7 核苷。Tri-O-acetylglucopyranurono-6,1-lactone 首次被用作 N-糖基化的糖基供体，并在与 1- 糖基化反应条件相似的反应条件下产生了 β-构型的 N9-和 N7-连接的嘌呤基葡萄糖醛酸苷。 O-乙酰基取代的糖基供体。评估了带有葡萄糖醛酸衍生物作为糖子的合成核苷的胆碱酯酶抑制谱，它们显示出中等的选择性乙酰胆碱酯酶抑制活性（Ki = 14.78–50.53 μM）。呋喃糖基
• Monocyclic L-nucleosides, analogs and uses thereof
  申请人：ICN Pharmaceuticals, Inc.

  公开号：US20020095033A1

  公开（公告）日：2002-07-18

  Novel monocyclic L-Nucleoside compounds have the general formula 1 Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.

  新型单环L-核苷化合物具有一般式1。这些化合物的实施被认为对治疗各种疾病有用，包括感染、寄生虫感染、肿瘤和自身免疫性疾病。从机理上看，这些新化合物的实施显示出免疫调节活性，并有望用于调节细胞因子模式，包括调节Th1和Th2反应。
• Synthesis and Glycosidic Reaction of 1,2-Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1080/07328309608005693

  日期：1996.9

  Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.
• EP1027359A4
  申请人：——

  公开号：EP1027359A4

  公开（公告）日：2001-07-25
• MONOCYCLIC L-NUCLEOSIDES, ANALOGS AND USES THEREOF
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1027359A2

  公开（公告）日：2000-08-16