6-amino-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose | 133587-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-amino-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose
• 英文别名: (1R)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-aminoethanol
• CAS: 133587-64-1
• 化学式: C₁₀H₁₉NO₅
• 分子量: 233.265
• InChiKey: SAUFBDKGNROEIY-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 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-amino-6-deoxy-1,2-O-isopropylidene-3-O-methyl-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35%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：

  1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 在 platinum(IV) oxide 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、133.32 Pa 条件下， 反应 169.0h， 生成 6-amino-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose
  参考文献：
  名称：

  Barton, Derek H. R.; Motherwell, William B., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1124 - 1131

  摘要：

  DOI：

文献信息

• One-pot synthesis of vicinal aminoalkanols from sugar aldehydes
  作者：Raquel G. Soengas、Artur M.S. Silva

  DOI：10.1016/j.tet.2013.02.072

  日期：2013.4

  A novel synthetic method of carbohydrate derived vicinal aminoalcohols, from sugar aldehydes and bromonitroalkanes, has been developed. It involves an indium-catalyzed one-pot Henry reaction and nitro group reduction, and proceeds with a remarkably high anti-selectivity. The reaction of the intermediate aminoalcohols with alkylating agents furnished the corresponding carbohydrate-based tertiary aminoalcohols

  从糖醛和溴硝基烷烃合成了一种新的碳水化合物衍生的邻氨基醇的合成方法。它涉及铟催化的一锅亨利反应和硝基还原，并以非常高的抗选择性进行。中间氨基醇与烷基化剂的反应为相应的基于碳水化合物的叔氨基醇提供了优异的立体选择性。这种非常简单的方法可以轻松地获得N，N-二烷基化邻氨基氨基链烷醇的家族，用于合成具有生物意义的衍生物和用于不对称催化的基于糖的立体分化剂的有用中间体。
• Intramolecular 6-<i>exo</i>-<i>dig</i> Post-Ugi Cyclization of N-Substituted 2-Alkynamides: Direct Access to Functionalized Morpholinone Glycoconjugates
  作者：Harikesh Kumar、Gurudayal Prajapati、Atul Dubey、Ravi Sankar Ampapathi、Pintu Kumar Mandal

  DOI：10.1021/acs.orglett.0c03486

  日期：2020.12.4

  We herein report a chemo- and regioselective 6-exo-dig catalytic cyclization of Ugi adducts N-substituted 2-alkynamides to access functionalized morpholinone glycoconjugates in the presence of triphenylphosphine. This array allows an interesting multicomponent access to a library of functionalized morpholinone glycoconjugates under mild reaction conditions with regeneration of catalyst triphenylphosphine, supported by ³¹P nuclear magnetic resonance studies. Density functional theory shows the 6-exo-dig oxocyclization pathway is preferred, which supports our experimental observation.
• Barton, Derek H. R.; Motherwell, William B., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1124 - 1131
  作者：Barton, Derek H. R.、Motherwell, William B.

  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.