6-benzylamino-O¹,O²-isopropylidene-6-deoxy-α-D-glucofuranose | 41341-82-6

• 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-benzylamino-O¹,O²-isopropylidene-6-deoxy-α-D-glucofuranose
• 英文别名: 6-Benzylamino-O¹,O²-isopropyliden-6-desoxy-α-D-glucofuranose；(3aR,5R,6S,6aR)-5-[(1R)-2-(benzylamino)-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 41341-82-6
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: BFOLRPODNFPAKB-XLWJZTARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  双(2-氯乙基)氨基磷酰二氯 、 6-benzylamino-O¹,O²-isopropylidene-6-deoxy-α-D-glucofuranose 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以28%的产率得到
  参考文献：
  名称：

  Preparation of Novel Cyclophosphamides Derivatives of Sugars

  摘要：

  Novel cyclophosphamide derivatives bearing a sugar structure were prepared by the treatment of the amino sugars from D-glucose and D-xylose with bis-(2-chloroethyl)aminophosphoric dichloride as well as with phosphoryl chloride and nucleophiles.

  DOI：

  10.3987/com-92-6211
• 作为产物：
  描述：

  苄胺 、 5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 生成 6-benzylamino-O¹,O²-isopropylidene-6-deoxy-α-D-glucofuranose
  参考文献：
  名称：

  Ohle et al., Chemische Berichte, 1936, vol. 69, p. 1636,1637

  摘要：

  DOI：

文献信息

• Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
  作者：Navnath B. Kalamkar、Vijay M. Kasture、Sanjay T. Chavan、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.tet.2010.08.060

  日期：2010.10

  An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane id is reported in 72% and 57% overall yields, respectively, from D-(+)-glucurono-gamma-lactone. Thus, D-glucuronolactone 2 on acetonide protection. DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-alpha-D-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-alpha-D-glucurono-6,3-lactone 3b gave trihydroxy-azepane id. Glycosidase inhibitory activity of 1c/1d was studied and id was found to be potent inhibitor of alpha-mannosidase and beta-galactosidase. (C) 2010 Elsevier Ltd. All rights reserved.
• Ohle et al., Chemische Berichte, 1936, vol. 69, p. 1636,1637
  作者：Ohle et al.

  DOI：——

  日期：——
• Preparation of Novel Cyclophosphamides Derivatives of Sugars
  作者：Mitsuji Yamashita、Chihiro Takahashi、Kuniaki Seo

  DOI：10.3987/com-92-6211

  日期：——

  Novel cyclophosphamide derivatives bearing a sugar structure were prepared by the treatment of the amino sugars from D-glucose and D-xylose with bis-(2-chloroethyl)aminophosphoric dichloride as well as with phosphoryl chloride and nucleophiles.