phenyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 847237-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 847237-65-4
• 化学式: C₂₁H₃₀O₁₁
• 分子量: 458.463
• InChiKey: PFISRCKWNYKKGD-DCFOZQKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  167.53
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 phenyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到phenyl 4-O-(3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 四甲基溴化铵 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 phenyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017