(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one | 163228-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aS,4R,6R,7R,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
• 英文别名: (3aS,4R,6R,7R,7aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-[[(2R,3S,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,4-dihydro-2H-pyran-4-yl]oxy]-7-hydroxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 163228-39-5
• 化学式: C₂₅H₄₆O₁₀Si₂
• 分子量: 562.805
• InChiKey: HIZWCXPUCWSCQT-IMWGDMARSA-N

物化性质

• 沸点：
  619.6±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose 、 (3aS,4R,6R,7R,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 在 2,6-二叔丁基吡啶 、 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 作用下， 生成 、
  参考文献：
  名称：

  Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides

  摘要：

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).

  DOI：

  10.1021/ja00126a011
• 作为产物：
  描述：

  1,5-anhydro-6-O-(tert-butyldimethylsilyl)-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 在 二甲基二环氧乙烷 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3aS,4R,6R,7R,7aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
  参考文献：
  名称：

  Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides

  摘要：

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).

  DOI：

  10.1021/ja00126a011

文献信息

• Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides
  作者：Samuel J. Danishefsky、Victor Behar、John T. Randolph、Kenneth O. Lloyd

  DOI：10.1021/ja00126a011

  日期：1995.5

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).