[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-azido-6-bromooxan-2-yl]methyl acetate | 132470-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-azido-6-bromooxan-2-yl]methyl acetate
• CAS: 132470-43-0
• 化学式: C₁₂H₁₆BrN₃O₇
• 分子量: 394.179
• InChiKey: ZXOSPWZOEWHIFW-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-azido-6-bromooxan-2-yl]methyl acetate 在 4 A molecular sieve 、 sodium methylate 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 3-azido-3-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  2,3-二叠氮-2,3-二脱氧-D-甘露糖的β-糖苷，一种罕见的细菌细胞壁构建单元的合成前体。

  摘要：

  合成2,3-二叠氮-2,3-二脱氧-β-D-甘露吡喃糖苷衍生物，以制备2,3-二乙酰氨基-2,3-二脱氧-D-甘露糖醛酸的β-糖苷，一种细菌的稀有部分。寡糖。制备了直接的糖基供体4,6-二-O-乙酰基-2,3-二氮杂-2,3-二脱氧-α-D-甘露吡喃糖基溴化物，并在糖基化反应中测试了其合成能力。还阐述了一种间接途径：将3-叠氮基-3-脱氧-β-D-吡喃葡萄糖苷转化为β-D-甘露吡喃糖苷。顺式邻二叠氮功能成功地耐受了轻度酸性水解，三苯甲基化，琼斯氧化，TEMPO氧化，乙酰分解和TiBr（4）溴化的条件。

  DOI：

  10.1021/ol0058893
• 作为产物：
  描述：

  3-azido-3-deoxy-D-glucose 在 吡啶 、 溴化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-azido-6-bromooxan-2-yl]methyl acetate
  参考文献：
  名称：

  2,3-二叠氮-2,3-二脱氧-D-甘露糖的β-糖苷，一种罕见的细菌细胞壁构建单元的合成前体。

  摘要：

  合成2,3-二叠氮-2,3-二脱氧-β-D-甘露吡喃糖苷衍生物，以制备2,3-二乙酰氨基-2,3-二脱氧-D-甘露糖醛酸的β-糖苷，一种细菌的稀有部分。寡糖。制备了直接的糖基供体4,6-二-O-乙酰基-2,3-二氮杂-2,3-二脱氧-α-D-甘露吡喃糖基溴化物，并在糖基化反应中测试了其合成能力。还阐述了一种间接途径：将3-叠氮基-3-脱氧-β-D-吡喃葡萄糖苷转化为β-D-甘露吡喃糖苷。顺式邻二叠氮功能成功地耐受了轻度酸性水解，三苯甲基化，琼斯氧化，TEMPO氧化，乙酰分解和TiBr（4）溴化的条件。

  DOI：

  10.1021/ol0058893

文献信息

• 3-Azido-3-deoxy-glycopyranoside derivatives as scaffolds for the synthesis of carbohydrate-Based universal pharmacophore mapping libraries
  作者：Rakesh Jain、Muthoni Kamau、Chunguang Wang、Robert Ippolito、Huiming Wang、Richard Dulina、Jan Anderson、David Gange、Michael J. Sofia

  DOI：10.1016/s0960-894x(03)00384-6

  日期：2003.7

  The regiospecific syntheses of six monosaccharide scaffolds, 1-6, containing a carboxylic acid, an azido and a free hydroxyl group were accomplished through the utilization of a key intermediate, namely, methyl 3-azido-3-deoxy-beta-D-glucopyranoside (10). Scaffold 2 was also used in generating combinatorial libraries using solid-phase methodologies.

  通过利用关键的中间体甲基3-叠氮基-3-脱氧-β-D-吡喃葡萄糖苷，完成了六个含有羧酸，叠氮基和游离羟基的单糖骨架1-6的区域特异性合成。 （10）。支架2还用于使用固相方法生成组合库。
• Glycorandomization and production of novel vancomycin analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20040259228A1

  公开（公告）日：2004-12-23

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。
• MARTIN, A.;MONNERET, C.;GAUTIER, C.;FOURNIER, J. P.;ROGER, P., J. CARBOHYDR. CHEM., 9,(1990) N, C. 853-861
  作者：MARTIN, A.、MONNERET, C.、GAUTIER, C.、FOURNIER, J. P.、ROGER, P.

  DOI：——

  日期：——
• Glycorandomization and Production of Novel Vancomycin Analogs
  申请人：Thorson Jon

  公开号：US20080268504A1

  公开（公告）日：2008-10-30

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.
• Glycorandomization and Production of Novel Novobiocin Analogs
  申请人：Thorson Jon

  公开号：US20120264924A1

  公开（公告）日：2012-10-18

  The present invention provides glycorandomized structures and combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.