2,3,4,6-tetra-O-benzyl-1-deoxy-1-(1'-hydroxy-propyl)-β-D-mannopyranose | 904324-84-1

• 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-1-deoxy-1-(1'-hydroxy-propyl)-β-D-mannopyranose
• 英文别名: (1S)-1-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propan-1-ol
• CAS: 904324-84-1
• 化学式: C₃₇H₄₂O₆
• 分子量: 582.737
• InChiKey: VFBCEIABBYTXLZ-WBEFEAJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-deoxy-1-(1'-hydroxy-propyl)-β-D-mannopyranose 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以80%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester
  参考文献：
  名称：

  Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization of C-Allyl Glycosides

  摘要：

  Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)(2)Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.

  DOI：

  10.1021/ol060671n
• 作为产物：
  描述：

  (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-propylidene-D-mannopyranose 在 硼烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.5h， 以43%的产率得到2,3,4,6-tetra-O-benzyl-1-deoxy-1-(1'-hydroxy-propyl)-β-D-mannopyranose
  参考文献：
  名称：

  Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization of C-Allyl Glycosides

  摘要：

  Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)(2)Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.

  DOI：

  10.1021/ol060671n