4-benzylamin-4-N-3-O-carbonyl-4,6-dideoxy-D-galactol | 1258284-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-benzylamin-4-N-3-O-carbonyl-4,6-dideoxy-D-galactol
• 英文别名: (3aS,4R,7aR)-3-benzyl-4-methyl-4,7a-dihydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1258284-48-8
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: LZSTVGJOGURXIX-RTXFEEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzylamin-4-N-3-O-carbonyl-4,6-dideoxy-D-galactol 在 sodium azide 、 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A novel glycosyl donor for synthesis of 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranosides

  摘要：

  2-Azido-4-benzylamino-4-N-,3-O-carbony1-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate (14) was conveniently prepared in six steps by regioselective introduction of an N-benzyl carbamate at O-3 of 6-deoxy-D-glucal 6, followed by mesylation at O-4. Intramolecular displacement of the leaving group afforded oxazolidinone 11. Azidonitration of the bicyclic glycal 11 gave the glycosyl nitrate anomers 12 in good yield and stereoselectivity. Hydrolysis of the anomeric nitrates under aqueous conditions gave the pyranose 13, which was easily converted into the imidate 14. Glycosylation of cyclohexanol by 14 gave glycosides 16 alpha and 16 beta in a ratio of 4:1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.017
• 作为产物：
  描述：

  3-O-(N-benzyl)-carbamoyl-6-deoxy-4-O-mesyl-D-glucal 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以95%的产率得到4-benzylamin-4-N-3-O-carbonyl-4,6-dideoxy-D-galactol
  参考文献：
  名称：

  A novel glycosyl donor for synthesis of 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranosides

  摘要：

  2-Azido-4-benzylamino-4-N-,3-O-carbony1-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate (14) was conveniently prepared in six steps by regioselective introduction of an N-benzyl carbamate at O-3 of 6-deoxy-D-glucal 6, followed by mesylation at O-4. Intramolecular displacement of the leaving group afforded oxazolidinone 11. Azidonitration of the bicyclic glycal 11 gave the glycosyl nitrate anomers 12 in good yield and stereoselectivity. Hydrolysis of the anomeric nitrates under aqueous conditions gave the pyranose 13, which was easily converted into the imidate 14. Glycosylation of cyclohexanol by 14 gave glycosides 16 alpha and 16 beta in a ratio of 4:1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.017

文献信息

• A novel glycosyl donor for synthesis of 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranosides
  作者：Ithayavani Iynkkaran、David R. Bundle

  DOI：10.1016/j.carres.2010.08.017

  日期：2010.11

  2-Azido-4-benzylamino-4-N-,3-O-carbony1-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate (14) was conveniently prepared in six steps by regioselective introduction of an N-benzyl carbamate at O-3 of 6-deoxy-D-glucal 6, followed by mesylation at O-4. Intramolecular displacement of the leaving group afforded oxazolidinone 11. Azidonitration of the bicyclic glycal 11 gave the glycosyl nitrate anomers 12 in good yield and stereoselectivity. Hydrolysis of the anomeric nitrates under aqueous conditions gave the pyranose 13, which was easily converted into the imidate 14. Glycosylation of cyclohexanol by 14 gave glycosides 16 alpha and 16 beta in a ratio of 4:1. (C) 2010 Elsevier Ltd. All rights reserved.