N-[(2S,3S,4S,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-iodo-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]benzenesulfonamide | 162128-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3S,4S,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-iodo-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]benzenesulfonamide
• CAS: 162128-75-8
• 化学式: C₆₉H₈₄INO₁₆SSi
• 分子量: 1370.48
• InChiKey: PIPGHABMQCUNKL-IBQSPTJXSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.39
• 重原子数：
  89
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-4-tributylstannyloxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-3-ol 、 N-[(2S,3S,4S,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-iodo-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]benzenesulfonamide 在 silver tetrafluoroborate 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到N-[(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-[[(2R,3R,4R)-3-hydroxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-4-yl]oxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Randolph, John T.; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1538 - 1541

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-三-O-苄基-L-吡喃岩藻糖基氟化物 在 tin(II) trifluoromethanesulfonate 、 2,6-二叔丁基吡啶 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 N-[(2S,3S,4S,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3-iodo-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]benzenesulfonamide
  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