(1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-nitrophenyl)-3-butene | 135865-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-nitrophenyl)-3-butene
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[[(1S)-1-(4-nitrophenyl)but-3-enyl]amino]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 135865-84-8
• 化学式: C₃₆H₅₄N₂O₁₁
• 分子量: 690.832
• InChiKey: CKZYNCUYFYRFCF-MUJQFDPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-tetrahydro-pyran-4-yl ester 、 烯丙基三甲基硅烷 在 四氯化锡 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-nitrophenyl)-3-butene
  参考文献：
  名称：

  Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines

  摘要：

  Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.

  DOI：

  10.1021/jo00020a033

文献信息

• Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines
  作者：Sabine Laschat、Horst Kunz

  DOI：10.1021/jo00020a033

  日期：1991.9

  Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.