Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-benzyloxycarbonylamino-6-phenoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester | 884525-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-benzyloxycarbonylamino-6-phenoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS: 884525-57-9
• 化学式: C₃₁H₃₃NO₁₁S
• 分子量: 627.669
• InChiKey: KGDAEIFXAVHVRV-WYQCABFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-benzyloxycarbonylamino-6-phenoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-azidomethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water

  摘要：

  A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

  DOI：

  10.1021/ja056253f
• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate 在 吡啶 、 甲醇 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-benzyloxycarbonylamino-6-phenoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water

  摘要：

  A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

  DOI：

  10.1021/ja056253f