2-cyanoethyl-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N,N'-diisopropylphosphoramidite | 1085304-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyanoethyl-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N,N'-diisopropylphosphoramidite
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a)-O-P(OCH2CH2CN)N(iPr)2；3-[[di(propan-2-yl)amino]-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyphosphanyl]oxypropanenitrile
• CAS: 1085304-11-5
• 化学式: C₄₃H₅₃N₂O₇P
• 分子量: 740.877
• InChiKey: AMYJWKNFCAPSPN-ZVNQLMPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide 、 (iPr2N)2PO(CH2)2CN 在 1,8-双二甲氨基萘 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以82%的产率得到2-cyanoethyl-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N,N'-diisopropylphosphoramidite
  参考文献：
  名称：

  Stereoselective Synthesis of α-Glycosyl Phosphites and Phosphoramidites via O-Selective Glycosylation of H-Phosphonate Derivatives

  摘要：

  A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various alpha-glycosyl phosphites; and phosphoramidites in a highly stereoselective manner with complete O-selectivity.

  DOI：

  10.1021/ol802190x