allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside | 165061-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside
• CAS: 165061-04-1
• 化学式: C₄₈H₅₇NO₂₃
• 分子量: 1015.97
• InChiKey: ALWJHHPKAUHCOR-OXNPZGMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  72.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  300.25
• 氢给体数：
  2.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-3-O-benzyl-D-mannopyranosyl trichloroacetimidate 、 allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到allyl 2-O-acetyl-3,6-bis-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside
  参考文献：
  名称：

  Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose

  摘要：

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.

  DOI：

  10.1016/0008-6215(94)00369-q
• 作为产物：
  描述：

  allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1<*>2)-4,6-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside 在 palladium on activated charcoal 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.83h， 生成 allyl 2-O-acetyl-3-O-<4,6-di-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-benzyl-α-D-mannopyranosyl>-α-D-mannopyranoside
  参考文献：
  名称：

  Enzymic transfer of 6-modified d-galactosyl residues: synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-d-galactose residues at the nonreducing end and evaluation of 6-deoxy-d-galactosyl transfer to glycoprotein using bovine β-(1 → 4)-galactosyltransferase and UDP-6-deoxy-d-galactose

  摘要：

  UDP-6-Deoxy-D-galactose and UDP-6-deoxy-6-fluoro-D-galactose were synthesized and their transfer to 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine) by beta-(1 --> 4)galactosyltransferase was examined. The transfer rates of 6-deoxy-D-galactose and 6-deoxy-6-fluoro-D-galactose were 1.3 and 0.2% of that of D-galactosyl transfer, respectively. The 2-acetamido-4-O-(6-deoxy-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranose (6'-deoxy-N-acetyllactosamine) and methyl 2-acetamido-4-O-(6-deoxy-6-fluoro-beta-D-galactopyranosyl)-2-deoxy-D-glucopyranoside (6'-deoxy-6'-fluoro-N-acetyllactosamine) were synthesized enzymatically in 30 and 59% yields, respectively. Further, 6-deoxy-D-galactose could be completely transferred to N-linked type biantennary oligosaccharides having two N-acetyl-D-glucosaminyl residues at the nonreducing end to give the corresponding penta- and hepta-saccharides in 55 and 57% yields, respectively. An assay of 6-deoxy-D-galactosyl transfer using asialo agalacto alpha(1)-acid glycoprotein as an acceptor suggested that 6-deoxy-D-galactose was transferred to about 30% of the N-acetyl-D-glucosaminyl residues in the N-linked oligosaccharides of the glycoprotein.

  DOI：

  10.1016/0008-6215(94)00369-q