allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside | 147577-17-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside
• CAS: 147577-17-1
• 化学式: C₃₃H₄₀O₁₃
• 分子量: 644.673
• InChiKey: TYCTVGVMAUAFBG-DXVCOPAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  154.51
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside 在 chromium(VI) oxide 、 硫酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Structures of the glycopeptidolipid antigens of serovars 25and 26 of the Mycobacterium aviumserocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins

  摘要：

  The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. avium serovar 26 has been characterized as O-(2,4-di-O-methyl-alpha-L-fucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding D-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26-1 and 26-2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of H-1-C-13 NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the D and L enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the D-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-galactopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose.

  DOI：

  10.1016/s0008-6215(92)84233-i
• 作为产物：
  描述：

  allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以62%的产率得到allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Structures of the glycopeptidolipid antigens of serovars 25and 26 of the Mycobacterium aviumserocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins

  摘要：

  The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. avium serovar 26 has been characterized as O-(2,4-di-O-methyl-alpha-L-fucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding D-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26-1 and 26-2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of H-1-C-13 NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the D and L enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the D-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-galactopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose.

  DOI：

  10.1016/s0008-6215(92)84233-i