(3aS,4R,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one | 159494-36-7

• 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,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
• 英文别名: (3aS,4R,6S,7R,7aR)-4-(((tert-Butyldiphenylsilyl)oxy)methyl)-6-(((2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yl)oxy)-7-hydroxytetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-2-one；(3aS,4R,6S,7R,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-[[(2R,3S,4R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]oxy]-7-hydroxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 159494-36-7
• 化学式: C₄₅H₅₄O₁₀Si₂
• 分子量: 811.089
• InChiKey: RESRYTPKJDWPKE-SLDPZQNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 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,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 在 4 A molecular sieve 、 silver perchlorate 、 Di-tert-butylpyridine 、 tin(ll) chloride 作用下， 生成 [(2S,3R,4R,5S,6S)-6-[[(2R,3S,4R)-3-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-5-benzoyloxy-6-methyl-3,4-bis(phenylmethoxy)oxan-2-yl]oxy-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl]oxy]-2-methyl-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
  参考文献：
  名称：

  Behar, Victor; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1536 - 1538

  摘要：

  DOI：
• 作为产物：
  描述：

  D-lactal 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS,4R,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(2R,3S,4R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yloxy]-7-hydroxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
  参考文献：
  名称：

  Behar, Victor; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1536 - 1538

  摘要：

  DOI：

文献信息

• Behar, Victor; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1536 - 1538
  作者：Behar, Victor、Danishefsky, Samuel J.

  DOI：——

  日期：——
• 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).