3-O-[(2'',3''-di-O-benzyl-4'',6''-O-benzylidene-β-D-galactopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-(4-methoxybenzyl)-sn-glycerol | 1114560-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-[(2'',3''-di-O-benzyl-4'',6''-O-benzylidene-β-D-galactopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-(4-methoxybenzyl)-sn-glycerol
• CAS: 1114560-42-7
• 化学式: C₇₃H₇₈O₁₅
• 分子量: 1195.41
• InChiKey: SXLPSKJFPQNJLW-SJSRFWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.33
• 重原子数：
  88.0
• 可旋转键数：
  31.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  138.45
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3-O-[(2'',3''-di-O-benzyl-4'',6''-O-benzylidene-β-D-galactopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-(4-methoxybenzyl)-sn-glycerol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.028
• 作为产物：
  描述：

  o-methoxycarbonylphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 、 3-O-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)-1,2-di-O-(4-methoxybenzyl)-sn-glycerol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 以28.7 mg的产率得到3-O-[(2'',3''-di-O-benzyl-4'',6''-O-benzylidene-β-D-galactopyranosyl)-(1->6)-(2',3',4'-tri-O-benzyl-β-D-galactopyranosyl)]-1,2-di-O-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.028