4-O-<4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranosyl>-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-<4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranosyl>-D-glucopyranose
• 英文别名: GlcA(b1-4)Glc(b1-4)Glc；(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₈H₃₀O₁₇
• 分子量: 518.426
• InChiKey: DGQCHXKZLMHWNO-NARVIOTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  286
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 8.0h， 以90%的产率得到4-O-<4-O-(β-D-glucopyranosyluronic acid)-β-D-glucopyranosyl>-D-glucopyranose
  参考文献：
  名称：

  Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8

  摘要：

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.

  DOI：

  10.1016/s0040-4020(01)82378-4

文献信息

• Synthesis of structural elements of the capsular polysaccharide of streptococcus pneumoniae type 8
  作者：Franciscus A.W. Koeman、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0040-4020(01)82378-4

  日期：1993.6

  The synthesis is reported of propyl 4-O-alpha-D-galactopyranosyl-beta-D-glucopyranosiduronic acid (25), 4-O-[4-O-(beta-D-glucopyranosyluronic acid)-beta-D-glucopyranosyl]-D-glucopyranose (34), and 4-O-(4-O-beta-D-glucopyranosyl-alpha-D-glucopyranosyl)-D-galactopyranose (38), each representing a structural element of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type 8, [-->4)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->4)-alpha-D-Galp-(1-->]n. 2,3-Di-O-benzyl-4,6-O-benzylidene-alpha-D-galactopyranosyl trichloroacetimidate (12) was coupled to allyl 2-0-acetyl-3-O-benzyl-6-0-trityl-beta-D-glucopyranoside (7) in dichloromethane-ether, using trimethylsilyl trifluoromethanesulfonate as a promoter, to give disaccharide derivative 20. Detritylation of 20, followed by oxidation and deprotection, afforded disaccharide propyl glycoside 25. Coupling of 2,3,4,6-tetra-0-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (8) to allyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (17) in dichloromethane, with trimethylsilyl trifluoromethanesulfonate as a promoter, resulted in trisaccharide derivative 26. Deacetylation of 26, followed by 6-O-tritylation, benzylation, detritylation, and oxidation gave a protected trisaccharide derivative (31), which, after deprotection, afforded 34. Coupling of allyl 2,3,6-tri-O-benzyl-beta-D-galactopyranoside (10) to 4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (19) in ether, with trimethylsilyl trifluoromethanesulfonate as a promoter, gave trisaccharide derivative 35. Deallylation of 35, followed by hydrogenolysis afforded 38.