p-methoxyphenyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 898826-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 898826-58-9
• 化学式: C₅₇H₅₂O₁₇
• 分子量: 1009.03
• InChiKey: FPZULACAXAHCGC-CKQXCYCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  74.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  196.11
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 2.0h， 生成 p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  A concise and practical synthesis of antigenic globotriose, α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc

  摘要：

  A concise and practical synthesis of the antigenic globotriose, alpha-D-Gal-(1 -> 4)-beta-D-Gal-(1 -> 4)-beta-D-Glc (13), was achieved by coupling of a monosaccharide donor, 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (4) with a disaccharide acceptor, p-methoxyphenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (8), followed by deprotection. In spite of the existence of a C-2-ester substituent capable of neighboring-group participation in the donor, the coupling gave exclusively the alpha-linkage in satisfactory yield. The acceptor 8 was readily obtained from selective 3-O-benzoylation of the galactosyl. ring of p-methoxyphenyl 2,6-di-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (7), which was prepared from p-methoxyphenyl beta-D-lactoside (5) via isopropylidenation, benzoylation, and deisopropylidenation. Donor 4 was obtained from p-methoxylphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside (1) via selective 4,6-di-O-debenzoylation, oxidative removal of 1-O-MP, benzylidenation, and trichloroacetimidate formation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.029
• 作为产物：
  描述：

  苯甲酰氯 、 4-甲氧苯基-4-O-(β-D-吡喃半乳糖酰基)-β-D-吡喃葡萄糖苷 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 、 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以67%的产率得到p-methoxyphenyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  A concise and practical synthesis of antigenic globotriose, α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc

  摘要：

  A concise and practical synthesis of the antigenic globotriose, alpha-D-Gal-(1 -> 4)-beta-D-Gal-(1 -> 4)-beta-D-Glc (13), was achieved by coupling of a monosaccharide donor, 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (4) with a disaccharide acceptor, p-methoxyphenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (8), followed by deprotection. In spite of the existence of a C-2-ester substituent capable of neighboring-group participation in the donor, the coupling gave exclusively the alpha-linkage in satisfactory yield. The acceptor 8 was readily obtained from selective 3-O-benzoylation of the galactosyl. ring of p-methoxyphenyl 2,6-di-O-benzoyl-beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (7), which was prepared from p-methoxyphenyl beta-D-lactoside (5) via isopropylidenation, benzoylation, and deisopropylidenation. Donor 4 was obtained from p-methoxylphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside (1) via selective 4,6-di-O-debenzoylation, oxidative removal of 1-O-MP, benzylidenation, and trichloroacetimidate formation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.029