1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol | 297747-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
• 英文别名: [(2R,3S,4S,5R,6R)-2-[(1S,2R,3R,4S,5R,6S)-3-hydroxy-2,4,5,6-tetrakis(phenylmethoxy)cyclohexyl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 297747-10-5
• 化学式: C₆₈H₆₈O₁₂
• 分子量: 1077.28
• InChiKey: LQTWDSVNOYVZJT-YBSQHBSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  80
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以83%的产率得到Benzoic acid (2R,3S,4S,5R,6R)-2-((1R,2S,3R,4R,5S,6S)-3-acetoxy-2,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Targeted Glycosyl Donor Delivery for Site-Selective Glycosylation^,1

  摘要：

  [GRAPHICS]n-Pentenyl ortho esters (NPOEs) and n-pentenyl glycosides (NPGs) are interconvertible glycosyl donors which are activated by reaction with halonium ions. In a series of cyclic syn-1,3-diols, NPOEs have been found to specifically glycosylate the equatorial-OH while the NPG glycosylates predominantly, but not exclusively, the axial-OR. When the cyclic diol acceptor is presented with equivalent amounts of an NPOE and an NPG in a three component reaction, a single, double-glycosylation product is obtained, which conforms to the foregoing preferences, presenting evidence for site-selective glycosylation.

  DOI：

  10.1021/ol0001214
• 作为产物：
  描述：

  1,3,4,5-Tetra-O-benzyl-D-myo-inositol 、 3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 在 N-碘代丁二酰亚胺 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以73%的产率得到1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
  参考文献：
  名称：

  Targeted Glycosyl Donor Delivery for Site-Selective Glycosylation^,1

  摘要：

  [GRAPHICS]n-Pentenyl ortho esters (NPOEs) and n-pentenyl glycosides (NPGs) are interconvertible glycosyl donors which are activated by reaction with halonium ions. In a series of cyclic syn-1,3-diols, NPOEs have been found to specifically glycosylate the equatorial-OH while the NPG glycosylates predominantly, but not exclusively, the axial-OR. When the cyclic diol acceptor is presented with equivalent amounts of an NPOE and an NPG in a three component reaction, a single, double-glycosylation product is obtained, which conforms to the foregoing preferences, presenting evidence for site-selective glycosylation.

  DOI：

  10.1021/ol0001214