(1R)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-cyanophenyl)-3-butene | 135866-07-8

• 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: (1R)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-cyanophenyl)-3-butene
• CAS: 135866-07-8
• 化学式: C₃₇H₅₄N₂O₉
• 分子量: 670.844
• InChiKey: JVCDBFUHRISXSM-SDPIAUFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  48.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  150.25
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-6-[(E)-(4-cyanophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate 、 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49%的产率得到(1S)-N-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-1-amino-1-(4-cyanophenyl)-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