2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl dimethyl phosphite

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl dimethyl phosphite
• 英文别名: dimethyl [(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] phosphite
• 化学式: C₃₆H₄₁O₈P
• 分子量: 632.69
• InChiKey: NKFCEJUKCPDRQP-FGZSBDNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (二乙基氨基)二甲氧基膦 、 2,3,4,6-四-O-苄基-D-吡喃半乳糖 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl dimethyl phosphite 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl dimethyl phosphite
  参考文献：
  名称：

  Glycosylation using glycosyl phosphite as a glycosyl donor

  摘要：

  Glycosylation using glycosyl phosphites as glycosyl donors in the presence of a Lewis acid such as ZnCl2 or ZnCl2-AgClO4 has afforded the glycosides including sialoglycosides in good yields.

  DOI：

  10.1016/s0040-4020(01)89683-6

文献信息

• Stereoselective Synthesis of α-Glycosyl Phosphites and Phosphoramidites via <i>O</i>-Selective Glycosylation of <i>H</i>-Phosphonate Derivatives
  作者：Fumiko Matsumura、Natsuhisa Oka、Takeshi Wada

  DOI：10.1021/ol802190x

  日期：2008.11.20

  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.
• Glycosylation using glycosyl phosphite as a glycosyl donor
  作者：Yutaka Watanabe、Chikara Nakamoto、Takashi Yamamoto、Shoichiro Ozaki

  DOI：10.1016/s0040-4020(01)89683-6

  日期：——

  Glycosylation using glycosyl phosphites as glycosyl donors in the presence of a Lewis acid such as ZnCl2 or ZnCl2-AgClO4 has afforded the glycosides including sialoglycosides in good yields.