Methyl 2,6-di-O-acetyl-3-O-trityl-β-D-galactopyranoside | 122926-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Methyl 2,6-di-O-acetyl-3-O-trityl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-5-acetyloxy-3-hydroxy-6-methoxy-4-trityloxyoxan-2-yl]methyl acetate
• CAS: 122926-89-0
• 化学式: C₃₀H₃₂O₈
• 分子量: 520.579
• InChiKey: BKNJKPMPXYNDSR-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,6-di-O-acetyl-3-O-trityl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 0.75h， 生成 Methyl 2,6-di-O-acetyl-3-O-trityl-β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z

文献信息

• BETANELI, V. I.;KRYAZHEVSKIX, I. A.;OTT, A. YA.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N, S. 217-230
  作者：BETANELI, V. I.、KRYAZHEVSKIX, I. A.、OTT, A. YA.、KOCHETKOV, N. K.

  DOI：——

  日期：——