(R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanol | 184776-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanol
• CAS: 184776-05-4
• 化学式: C₂₂H₃₆O₁₁
• 分子量: 476.521
• InChiKey: WRMFTNFMTHJQJS-BENXPVAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanol 在 吡啶 、 氯化亚砜 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 (3aR,5S,6S,6aR)-6-[(R)-2-Benzyloxy-2-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethoxy]-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Synthesis of Ether Linked Pseudo-OligosaccharidesVia5,6-Cyclic Sulfate Derivatives of Protected Manno and Glucofuranose

  摘要：

  C-6 ring opening of 5,6-cyclic sulfate derivatives of protected manno and glucofuranose with carbohydrate alkoxides gave ether linked pseudo-di or trisaccharides. Use of methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 led to protected pseudo-disaccharide D-Glcf-(3-->6)-D-Manf-(5-->6)-D-Manf 4 and protected pseudo-trisaccharide D-Manf-(6-->3)-D-Glcf-(6-->3)-D-Glcf 11 derivatives in 66% and 41% overall yields, respectively.

  DOI：

  10.1080/07328309708005739
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-α-D-mannofuranoside 、 Lithium; (3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-olate 在 硫酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以70%的产率得到(R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethanol
  参考文献：
  名称：

  Synthesis of Ether Linked Pseudo-OligosaccharidesVia5,6-Cyclic Sulfate Derivatives of Protected Manno and Glucofuranose

  摘要：

  C-6 ring opening of 5,6-cyclic sulfate derivatives of protected manno and glucofuranose with carbohydrate alkoxides gave ether linked pseudo-di or trisaccharides. Use of methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 led to protected pseudo-disaccharide D-Glcf-(3-->6)-D-Manf-(5-->6)-D-Manf 4 and protected pseudo-trisaccharide D-Manf-(6-->3)-D-Glcf-(6-->3)-D-Glcf 11 derivatives in 66% and 41% overall yields, respectively.

  DOI：

  10.1080/07328309708005739