benzyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 18404-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 18404-77-8
• 化学式: C₄₅H₅₈O₂₆
• 分子量: 1014.94
• InChiKey: GLYUOTIPWZSNSP-XTCQWWFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  71.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  318.38
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  benzyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 palladium on activated charcoal 甲醇 、 氢气 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 3'-galactosyl-lactose
  参考文献：
  名称：

  Identification and synthesis of a trisaccharide produced from lactose by transgalactosylation

  摘要：

  Enzymatic transgalactosylation of lactose by means of Streptococcus thermophilus, subspecies DN-001065, led to a mixture of D-galactose (similar to 4%), D-glucose ( similar to 15%), lactose (similar to 51%), minor disaccharides (6%), trisaccharides ( similar to 20%) and tetrasaccharides (3%). The major trisaccharide ( similar to 16%) was identified by NMR spectroscopy and chemical synthesis as bring the known beta-D-galactopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-D-glucose (3'-beta-D-galactopyranosyl-lactose). It was purified from a mixture of peracetylated oligosaccharides by column chromatography followed by deacetylation. For the first time, 3'-beta-D-galactopyranosyl-lactose has been obtained on the 1 g scale, by resorting to simple techniques and equipment. NMR spectra have been unambiguously assigned. (C) 3000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00309-2
• 作为产物：
  描述：

  benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 benzyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Identification and synthesis of a trisaccharide produced from lactose by transgalactosylation

  摘要：

  Enzymatic transgalactosylation of lactose by means of Streptococcus thermophilus, subspecies DN-001065, led to a mixture of D-galactose (similar to 4%), D-glucose ( similar to 15%), lactose (similar to 51%), minor disaccharides (6%), trisaccharides ( similar to 20%) and tetrasaccharides (3%). The major trisaccharide ( similar to 16%) was identified by NMR spectroscopy and chemical synthesis as bring the known beta-D-galactopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->4)-D-glucose (3'-beta-D-galactopyranosyl-lactose). It was purified from a mixture of peracetylated oligosaccharides by column chromatography followed by deacetylation. For the first time, 3'-beta-D-galactopyranosyl-lactose has been obtained on the 1 g scale, by resorting to simple techniques and equipment. NMR spectra have been unambiguously assigned. (C) 3000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00309-2