N-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside | 299409-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside
• 英文别名: N-[(1R)-1-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]prop-2-enyl]-N-benzylhydroxylamine
• CAS: 299409-46-4
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: UTJBMXMSTXVETK-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside 在 copper diacetate 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以80%的产率得到5-benzylamino-5-deoxy-5-vinyl-2,3-O-isopropylidene-1-O-methyl-α-D-manno-1,4-pentofuranoside
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449
• 作为产物：
  描述：

  乙烯基溴化镁 、 (Z)-N-(5-deoxy-2,3-0-isopropylidene-l-O-methyl-D-yxo-l,4-furanose-5-ylidene)benzylamine N-oxide 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到N-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-2,3-O-isopropylidene-1-O-methyl-β-L-gulo-1,4-pentofuranoside
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449