N-isopropyl-D-glucosamine | 13996-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-isopropyl-D-glucosamine
• 英文别名: 2-methyl-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]propanamide
• CAS: 13996-78-6
• 化学式: C₁₀H₁₉NO₆
• 分子量: 249.264
• InChiKey: KXTUJUVCAGXOBN-OXNFMAJFSA-N

物化性质

• 沸点：
  570.7±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-isopropyl-D-glucosamine 在 sodium tetrahydroborate 作用下， 生成 2-deoxy-2-isobutyramido-D-glucitol
  参考文献：
  名称：

  2-deoxy-1,3,4,5,6-penta-O-methyl-2-(N-methylacetamido)-d-glucitol and derivatives undergo C-emthylation at the N-methylacetamido group on repeated hakomori methylation

  摘要：

  DOI：

  10.1016/s0008-6215(00)90289-1
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 、 异丁酸酐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到N-isopropyl-D-glucosamine
  参考文献：
  名称：

  Palladium-catalysed asymmetric allylic alkylation using new chiral phosphinite–nitrogen ligands derived from D-glucosamine

  摘要：

  由D-葡萄糖胺合成的新型亚磷酰胺-氮手性配体，在钯催化烯丙基烷基化反应中表现出高度的非对映过量（高达96% ee）。

  DOI：

  10.1039/a810041a

文献信息

• Palladium-catalysed asymmetric allylic alkylation using new chiral phosphinite–nitrogen ligands derived from D-glucosamine
  作者：Koji Yonehara、Tomohiro Hashizume、Kenji Mori、Kouichi Ohe、Sakae Uemura

  DOI：10.1039/a810041a

  日期：——

  Novel phosphinite–nitrogen chiral ligands synthesized from D-glucosamine furnish a high level of enantiomeric excess (up to 96% ee) in palladium-catalysed allylic alkylation.

  由D-葡萄糖胺合成的新型亚磷酰胺-氮手性配体，在钯催化烯丙基烷基化反应中表现出高度的非对映过量（高达96% ee）。
• Amphetamine Prodrugs
  申请人：Shire AG

  公开号：US20140073589A1

  公开（公告）日：2014-03-13

  The present invention relates to amphetamine prodrugs which provide colonic release of amphetamine.

  本发明涉及一种安非他命前药，其提供安非他命的结肠释放。
• Palladium-Catalyzed Asymmetric Allylic Substitution Reactions Using New Chiral Phosphinite−Oxazoline Ligands Derived from <scp>d</scp>-Glucosamine
  作者：Koji Yonehara、Tomohiro Hashizume、Kenji Mori、Kouichi Ohe、Sakae Uemura

  DOI：10.1021/jo990901u

  日期：1999.12.1

  Novel 8-alkyl- or 2-aryl-4,5-(4,6-O-benzylidene-3-O-(diphenylphosphino)-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazolines (5a-f) have been prepared from D-glucosamine hydrochloride. They work effectively as chiral ligands and provide a high level of enantiomeric excess in palladium-catalyzed allylic alkylation and amination reactions. The allylic alkylation of 1,3-diphenyl-3-acetoxyprop-1-ene with dimethyl malonate proceeds smoothly in the presence of 0.25 mol % [Pd(eta(3)-C3H5)Cl](2) and the chiral ligand 5a having the smallest substituent on oxazoline at 0 degrees C within 6 h to furnish the highest enantiomeric excess (96% ee). The Ligand 5a is also effective for the Pd-catalyzed amination of ethyl 1,3-diphenylprop-2-enyl carbonate, leading to the corresponding allylic amine in 94% ee. The full scope and limitations using ligands 5a-f in the allylic substitution reactions are described.
• 2-deoxy-1,3,4,5,6-penta-O-methyl-2-(N-methylacetamido)-d-glucitol and derivatives undergo C-emthylation at the N-methylacetamido group on repeated hakomori methylation
  作者：Ulrich Zähringer、Ernst Theodor Rietschel

  DOI：10.1016/s0008-6215(00)90289-1

  日期：1986.9