1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose | 83562-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose
• 英文别名: 1-O-acetyl-2,3,4-tri-O-benzyl-α-L-fucopyranose；[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] acetate
• CAS: 83562-59-8
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: OOQYKGWPDLNECP-QLDZXNTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R,6S)-2-iodo-6-methyl-3,4,5-tris(phenylmethoxy)oxane
  参考文献：
  名称：

  Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

  摘要：

  alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.159
• 作为产物：
  描述：

  乙酸酐 、 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 吡啶 作用下， 反应 4.0h， 以85%的产率得到1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose
  参考文献：
  名称：

  Oligosaccharides from "standardized intermediates." Synthesis of a branched tetrasaccharide glycoside related to the blood group B determinant

  摘要：

  DOI：

  10.1021/ja00389a061

文献信息

• Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
  作者：Christine Wiebe、Claudine Schlemmer、Stefan Weck、Till Opatz

  DOI：10.1039/c1cc13078a

  日期：——

  Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

  单糖基和二糖基修饰的芳香化合物和杂芳香化合物可作为构建代谢稳定的低聚糖模拟物的砌块。本文描述了通过直接C-糖基化、偶极环加成或Larock环化反应从单糖前体合成这些化合物的方法。
• The role of sugar configuration in the acetolysis of 6-deoxyhexose methyl glycosides
  作者：Luigi Cirillo、Annalida Di Nola、Emiliano Bedini、Michelangelo Parrilli

  DOI：10.1016/j.carres.2009.08.037

  日期：2009.11

  equiv ZnCl(2) in 2:1 v/v Ac(2)O-AcOH at 5 degrees C; 10:10:1 v/v/v Ac(2)O-AcOH-TFA at 70 degrees C) was studied. We focused on the effect of sugar configuration on the competition between mechanisms with activation at exocyclic or endocyclic oxygen site. No effect was detected in acetolysis using the TFA protocol promoting an exo-activation mechanism, which affords 1-O-Ac-pyranosides regardless of sugar

  在两个温和的条件下（5当量10：10：1 v / v Ac（2）O-AcOH; 10：10：1 v / v / v中的10个当量ZnCl（2）在两个温和的条件下乙酰化几个过苄基的6-脱氧己糖甲基糖苷研究了在70摄氏度下的Ac（2）O-AcOH-TFA）。我们专注于糖构型对环外或环内氧位点激活机制之间竞争的影响。使用TFA方案促进外泌激活机制的乙酰分解没有发现任何作用，该机制可提供1-O-Ac-吡喃糖苷，而与糖的构型无关。相反，它在确定ZnCl（2）促进的乙解中的内-外-产品分布上具有主要作用。
• 2′-Deoxy-2′-alkoxylaminouridines: Novel 2′-substituted uridines prepared by intramolecular nucleophilic ring opening of 2,2′-O-anhydrouridines
  作者：David P. Sebesta、Sarah S. O'Rourke、Rogelio L. Martinez、Wolfgang A. Pieken、Danny P.C. McGee

  DOI：10.1016/0040-4020(96)00870-8

  日期：1996.11

  methodology developed for the stereo- and regiospecific introduction of structural modifications at the 2′-position of uridine nucleosides. A novel class of modified nucleosides, 2′-alkoxylamino-2′-deoxy uridines, are prepared by intramolecular nucleophilic addition of a 3′-tethered alkoxycarbamate nucleophile to the 2′-position with concomitant opening of a 2,2′-anhydrouridine.

  天然和非天然修饰的核苷和核苷酸在生物学，医学和生物医学研究工具中都起着重要作用。本文报道的是开发用于在尿苷核苷的2'-位立体和区域特异性引入结构修饰的合成方法的应用。一类新的修饰核苷，即2'-烷氧基氨基-2'-脱氧尿苷，是通过将3'-拴链的烷氧基氨基甲酸酯亲核体分子内亲核加成到2'-位置，并同时打开2,2'-脱水尿苷来制备的。
• The sequential double aryl C-glycosidation: Introduction of a second sugar unit onto mono aryl C-glycosides using
  作者：Takeshi Kuribayashi、Nobuyuki Ohkawa、Susumu Satoh

  DOI：10.1016/s0040-4039(98)00826-0

  日期：1998.6

  The promoter combination (SnCl4/AgOTfa) was successfully applied to introduce a second sugar unit onto mono aryl C-glycosides. A systematic survey of this sequential double aryl C-glycosidation is described. (C) 1998 Elsevier Science Ltd. AII rights reserved.