2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖 6-乙酸酯 | 157896-03-2

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖 6-乙酸酯
• 中文别名: 2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖6-乙酸酯
• 英文名称: 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose
• 英文别名: 2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-beta-D-glucopyranose 6-acetate；[(2R,3S,4R,5R,6R)-5-azido-6-hydroxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 157896-03-2
• 化学式: C₂₂H₂₅N₃O₆
• 分子量: 427.457
• InChiKey: GKZFEMRXZMCDPE-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖 6-乙酸酯 在 chromium(VI) oxide 、 硫酸 、 叔丁基二甲硅基三氟甲磺酸酯 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 35.5h， 生成 allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8
• 作为产物：
  描述：

  thexyldimethylsilyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 2-叠氮基-2-脱氧-3,4-二-O-苄基-beta-D-吡喃葡萄糖 6-乙酸酯
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8

文献信息

• [EN] AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM<br/>[FR] PROCÉDÉ EFFICACE ET EXTENSIBLE DE FABRICATION DE FONDAPARINUX SODIQUE
  申请人：RELIABLE BIOPHARMACEUTICAL CORP

  公开号：WO2013115817A1

  公开（公告）日：2013-08-08

  The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

  本发明涉及一种用于合成因子Xa抗凝剂Fondaparinux及相关化合物的过程。此外，该发明还涉及用于合成Fondaparinux及相关化合物的各种中间体的高效可扩展过程。
• EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
  申请人：Patel Payal P.

  公开号：US20120116066A1

  公开（公告）日：2012-05-10

  The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.

  本发明涉及一种合成因子Xa抗凝剂Fondaparinux及相关化合物的方法。此外，该发明还涉及一种高效且可扩展的合成过程，用于合成Fondaparinux及相关化合物中有用的各种中间体。
• PROCESS FOR PREPARING FONDAPARINUX SODIUM AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
  申请人：Nadji Sourena

  公开号：US20110105418A1

  公开（公告）日：2011-05-05

  Processes for the synthesis of the Factor Xa anticoagulent Fondaparinux, and related compounds are described. Also described are protected pentasaccharide intermediates as well as efficient and scalable processes for the industrial scale production of Fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions.

  描述了合成抗凝血因子Xa的抗凝剂Fondaparinux及其相关化合物的过程。还描述了受保护的五糖中间体，以及通过一系列去保护和磺化反应将受保护的五糖中间体转化为Fondaparinux钠的高效可扩展工业规模生产过程。
• A Synthetic Approach to Aromatic Aminoglycoside as a Neamine Mimic
  作者：Takashi Yamanoi、Ryo Inoue、Sho Matsuda、Yoshiki Oda、Hirofumi Ooyama、Akihiro Yoshida、Keita Hamasaki

  DOI：10.3987/com-11-s(p)69

  日期：——

  This paper describes the synthetic approach to an aromatic alpha-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyloxy)-1,3-phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.
• An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics
  作者：Carlos Jaramillo、Jose-Luis Chiara、Manuel Martin-Lomas

  DOI：10.1021/jo00090a035

  日期：1994.6

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.