phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside | 299174-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside
• 英文别名: 4-oxo-4-[(2S,3R,4S,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylsulfanyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]oxybutanoic acid
• CAS: 299174-99-5
• 化学式: C₆₄H₆₆O₁₃S
• 分子量: 1075.29
• InChiKey: ATNSBYBPDHHECC-IGJQKXJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  78
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 、 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以61%的产率得到phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-[3-(2-O-benzoyl-1-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-3-yloxycarbonyl)propanoyl]-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113

文献信息

• Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors
  作者：Gregor Lemanski、Thorsten Lindenberg、Hassan Fakhrnabavi、Thomas Ziegler

  DOI：10.1080/07328300008544113

  日期：2000.1

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.