(1R,3R,3aS)-3-phenyl-1-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole | 1401990-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,3aS)-3-phenyl-1-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole
• CAS: 1401990-02-0
• 化学式: C₄₅H₄₈NO₇P
• 分子量: 745.852
• InChiKey: VAGLZSOUKQBAIS-SUBDKAMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,3R,3aS)-3-phenyl-1-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole 、 phenyl 2,3,4-tri-O-benzoyl-β-D-thioglucopyranoside 在 N-氰甲基吡咯烷鎓三氟甲烷磺酸盐 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Stereoselective Synthesis of P-Modified α-Glycosyl Phosphates by the Oxazaphospholidine Approach

  摘要：

  alpha-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural alpha-glycosyl phosphates including "P-modified analogs" have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the intersugar phosphorus atom in alpha-glycosyl phosphates by use of the oxazaphospholidine method is presented. Via this approach, the dimers of alpha-glycosyl phosphorothioates and alpha-glycosyl boranophosphates were obtained efficiently and stereoselectively.

  DOI：

  10.1021/ol402785h
• 作为产物：
  描述：

  (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol 在 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (1R,3R,3aS)-3-phenyl-1-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole
  参考文献：
  名称：

  Stereoselective Synthesis of P-Modified α-Glycosyl Phosphates by the Oxazaphospholidine Approach

  摘要：

  alpha-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural alpha-glycosyl phosphates including "P-modified analogs" have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the intersugar phosphorus atom in alpha-glycosyl phosphates by use of the oxazaphospholidine method is presented. Via this approach, the dimers of alpha-glycosyl phosphorothioates and alpha-glycosyl boranophosphates were obtained efficiently and stereoselectively.

  DOI：

  10.1021/ol402785h

文献信息

• Stereoselective Synthesis of <i>P</i>-Modified α-Glycosyl Phosphates by the Oxazaphospholidine Approach
  作者：Mihoko Noro、Shoichi Fujita、Takeshi Wada

  DOI：10.1021/ol402785h

  日期：2013.12.6

  alpha-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural alpha-glycosyl phosphates including "P-modified analogs" have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the intersugar phosphorus atom in alpha-glycosyl phosphates by use of the oxazaphospholidine method is presented. Via this approach, the dimers of alpha-glycosyl phosphorothioates and alpha-glycosyl boranophosphates were obtained efficiently and stereoselectively.