6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol | 155696-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol
• 英文别名: (2R,3R,4R,5R)-6-azido-3,4-bis(phenylmethoxy)hexane-1,2,5-triol
• CAS: 155696-77-8
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: MQNUZBMJDIGYPL-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol 在 palladium on activated charcoal 盐酸 、 氢气 、 溴 、 三丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 49.5h， 生成 1-甘露糖野尻霉素盐酸盐
  参考文献：
  名称：

  An efficient conversion of d-mannitol into d-fructose and 1,5-dideoxy-1,5-imino-d-mannitol (1-deoxymannojirimycin)

  摘要：

  The utility of bis(tributyltin)oxide-bromine for the selective oxidation of secondary hydroxyl groups in the presence of primary hydroxyl groups has been further demonstrated by the efficient conversions of D-mannitol into D-fructose and 1,5-dideoxy-1,5-imino-D-mannitol (1-deoxymannojirimycin).

  DOI：

  10.1016/0008-6215(94)84240-x
• 作为产物：
  描述：

  3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 在 吡啶 、 sodium azide 、 溶剂黄146 、 对甲苯磺酰氯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol
  参考文献：
  名称：

  An efficient conversion of d-mannitol into d-fructose and 1,5-dideoxy-1,5-imino-d-mannitol (1-deoxymannojirimycin)

  摘要：

  The utility of bis(tributyltin)oxide-bromine for the selective oxidation of secondary hydroxyl groups in the presence of primary hydroxyl groups has been further demonstrated by the efficient conversions of D-mannitol into D-fructose and 1,5-dideoxy-1,5-imino-D-mannitol (1-deoxymannojirimycin).

  DOI：

  10.1016/0008-6215(94)84240-x

文献信息

• Synthesis and conformational studies of 3,4-di-O-acylated furanoid sugar amino acid-containing analogs of the receptor binding inhibitor of vasoactive intestinal peptide
  作者：T.K. Chakraborty、S. Uday Kumar、B. Krishna Mohan、G. Dattatreya Sarma、M. Udaya Kiran、B. Jagadeesh

  DOI：10.1016/j.tetlet.2007.07.158

  日期：2007.9

  Structural analysis of the di-O-caprylated Gaa-containing analog of the receptor binding inhibitors of vasoactive intestinal peptide by various NMR techniques and constrained molecular dynamics (XID) simulation studies established a well-defined beta-turn structure in DMSO-d(6) with an intramolecular hydrogen bond between TyrNH -> MetCO. (c) 2007 Elsevier Ltd. All rights reserved.
• An efficient conversion of d-mannitol into d-fructose and 1,5-dideoxy-1,5-imino-d-mannitol (1-deoxymannojirimycin)
  作者：Wei Zou、Walter A. Szarek

  DOI：10.1016/0008-6215(94)84240-x

  日期：1994.2

  The utility of bis(tributyltin)oxide-bromine for the selective oxidation of secondary hydroxyl groups in the presence of primary hydroxyl groups has been further demonstrated by the efficient conversions of D-mannitol into D-fructose and 1,5-dideoxy-1,5-imino-D-mannitol (1-deoxymannojirimycin).