methyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 96961-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 2-azido-3,4-di-0-benzyl-2-deoxy-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-azido-6-methoxy-3,4-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 96961-21-6
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: DGQQGHISWOSILJ-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 silver zeolite 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 [(2R,3S,4R,5R,6S)-5-Azido-6-((2R,3S,4R,5R,6R)-5-azido-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-3-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol
  参考文献：
  名称：

  Synthesis of two analogues of Rhodomicrobium vannielii Lipid A

  摘要：

  DOI：

  10.1016/0008-6215(85)85173-9
• 作为产物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl bromide 在 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two analogues of Rhodomicrobium vannielii Lipid A

  摘要：

  DOI：

  10.1016/0008-6215(85)85173-9

文献信息

• Disaccharide and trisaccharide derivatives of the "Lipid A" type
  申请人：Akzo N.V.

  公开号：US04719202A1

  公开（公告）日：1988-01-12

  The present invention is dealing with certain disaccharide or trisaccharide derivatives of the lipid A type, which have interesting immuno-modulating, more particularly immuno-stimulating properties.

  本发明涉及一种具有有趣的免疫调节，更具体地说是免疫刺激性能的脂多糖A型的某些二糖或三糖衍生物。
• Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride
  作者：Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0008-6215(01)00078-7

  日期：2001.5

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.
• WESTERDUIN, P.;BEETZ, T.;DEES, M. J.;ERKELENS, C.;SMID, P.;ZUURMOND, H.;V+, J. CARBOHYDR. CHEM., 7,(1988) N 3, C. 617-644
  作者：WESTERDUIN, P.、BEETZ, T.、DEES, M. J.、ERKELENS, C.、SMID, P.、ZUURMOND, H.、V+

  DOI：——

  日期：——
• Novel disaccharide and trisaccharide derivatives of the "Lipid A" type
  申请人：AKZO N.V.

  公开号：EP0192296B1

  公开（公告）日：1988-12-28