4-O-α-D-galactopyranosyl-α-D-glucopyranose | 208114-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-α-D-galactopyranosyl-α-D-glucopyranose
• 英文别名: Gal(a1-4)a-Glc；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 208114-77-6
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: GUBGYTABKSRVRQ-PIRXJBDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 72.0h， 生成 α-D-galactopyranosyl-(1->4)-β-D-glucopyranose 、 4-O-α-D-galactopyranosyl-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of 4′-O-acetyl-maltose and α-d-galactopyranosyl-(1→4)-d-glucopyranose for biochemical studies of amylose biosynthesis

  摘要：

  The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4'-OH group or by reversing its configuration, is reported. For synthesis of the 4'-O-acetylated analog, p-maltose was converted into its per-O-benzylated-4',6'-O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6'. Acetylation at C-4' of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra-O-benzyl-alpha/beta -D-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-tri-O-benzyl-1-thio-beta -D-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00306-2

文献信息

• JPH07304699A
  申请人：——

  公开号：JPH07304699A

  公开（公告）日：1995-11-21