(2R,3R,4R,5R,6S)-6-(((2R,3S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)oxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate | 1046134-94-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4R,5R,6S)-6-(((2R,3S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)oxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: O-(2-deoxy-2-azido-3,4,6-tri-O-Ac-α-D-galactopyranosyl)-N-Fmoc-L-threonine methyl ester
• CAS: 1046134-94-4
• 化学式: C₃₂H₃₆N₄O₁₂
• 分子量: 668.657
• InChiKey: ABZQNIDLQGFFCV-IWLIAURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  210.75
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  Fmoc-Thr-OMe 、 苯基硒基-2-叠氮基-3,4,6-三-O-乙酰基-α-D-吡喃半乳糖苷 在 碘 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 O-(2-deoxy-2-azido-3,4,6-tri-O-Ac-β-D-galactopyranosyl)-N-Fmoc-L-threonine methyl ester 、 (2R,3R,4R,5R,6S)-6-(((2R,3S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)oxy)-2-(acetoxymethyl)-5-azidotetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

  摘要：

  The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn, with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding alpha-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac(3)GalNAc-alpha-Ser)(3)-Gly and (Ac(3)GalNAc-alpha-Thr)(3)-Gly in 27% and 49% overall yield, respectively. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.03.034

文献信息

• A catalytic Koenigs-Knorr glycosylation based on acceptor activation with In(NTf2)3
  作者：Changwei Li、Haijing Liang、Zhan-xin Zhang、Zhaoyan Wang、Lan Yu、Huanxiang Liu、Fengli An、Shaohua Wang、Lixia Ma、Weihua Xue

  DOI：10.1016/j.tet.2018.05.080

  日期：2018.7

  important for gaining better insight into biological processes of significance to medicinal chemistry. Herein, we describe an In(NTf2)3 -catalyzed Koenigs-Knorr glycosylation based on the activation of an alcoholic hydroxyl group. A catalytic amount of In(NTf2)3 enables effective glycosylation of diverse alcohols with peracylated aldosyl bromides as donors, leading to the stereoselective formation of a series

  有效的糖基化方法的开发对于更好地了解对药物化学具有重要意义的生物学过程至关重要。在本文中，我们描述了基于醇羟基的活化的In（NTf 2）3催化的Koenigs-Knorr糖基化。催化量的In（NTf 2）3使用过酰基化的醛糖基溴作为供体，可以使各种醇类有效糖基化，从而以令人满意的收率立体选择性地形成一系列糖苷。该方案的特点是反应条件温和，官能团耐受性好，同时不需要任何添加剂。而且，这种转化的潜在效用通过重要的药用相关生物分子合成的便捷合成得到了证明。