allyl 2-O-methyl-α-L-fucopyranosyl-(1-> 2)-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-methyl-α-L-fucopyranosyl-(1-> 2)-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-β-D-galactopyranoside
• 英文别名: Fuc2Me(a1-2)Gal(b1-3)GalNAc(b)-O-allyl；N-[(2R,3R,4R,5R,6R)-4-[(2R,3R,4S,5R,6R)-3-[(2S,3S,4R,5S,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-prop-2-enoxyoxan-3-yl]acetamide
• 化学式: C₂₄H₄₁NO₁₅
• 分子量: 583.587
• InChiKey: GVIRSVICESBMFG-TVZGOCKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  235
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  半胱胺盐酸盐 、 allyl 2-O-methyl-α-L-fucopyranosyl-(1-> 2)-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-β-D-galactopyranoside 以 水 为溶剂， 反应 4.0h， 以70%的产率得到3-(2-aminoethylthiopropyl) 2-O-methyl-α-L-fucopyranosyl-(1-> 2)-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-β-D-galactopyranoside hydrochloride
  参考文献：
  名称：

  Synthesis of neoglycoproteins containing O-methylated trisaccharides related to excretory/secretory antigens of Toxocara larvae

  摘要：

  The disaccharides allyl beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 10a and 10b and the trisaccharides allyl 2-O-methyl-alpha-L-fucopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1--> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 18a and 18b have been prepared using stepwise assembly of the sugar units. The glycosidic linkages were formed employing the trichloroacetimidate procedure for the attachment of the galactopyranosyl residue and N-iodosuccinimide/triflic acid activation of an ethyl 1-thiofucopyranoside donor for fucosylation. Deprotection furnished the allyl glycosides which were converted into cysteamine-spacered ligands, activated with thiophosgene and subsequently linked to bovine serum albumin. The neoglycoproteins serve as immunoreagents to determine epitope specificities of monoclonal antibodies directed against highly immunogenic O-glycans located at the surface of Toxocara larvae. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00355-5
• 作为产物：
  描述：

  allyl 3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl-(1-> 2)-4,6-di-O-acetyl-3-O-benzoyl-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-4,6-di-O-pivaloyl-β-D-galactopyranoside 在 sodium methylate 、 四丁基氢氧化铵 作用下， 以 甲醇 、 1,4-二氧六环 、 水 为溶剂， 反应 13.0h， 以82%的产率得到allyl 2-O-methyl-α-L-fucopyranosyl-(1-> 2)-β-D-galactopyranosyl-(1-> 3)-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neoglycoproteins containing O-methylated trisaccharides related to excretory/secretory antigens of Toxocara larvae

  摘要：

  The disaccharides allyl beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 10a and 10b and the trisaccharides allyl 2-O-methyl-alpha-L-fucopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1--> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 18a and 18b have been prepared using stepwise assembly of the sugar units. The glycosidic linkages were formed employing the trichloroacetimidate procedure for the attachment of the galactopyranosyl residue and N-iodosuccinimide/triflic acid activation of an ethyl 1-thiofucopyranoside donor for fucosylation. Deprotection furnished the allyl glycosides which were converted into cysteamine-spacered ligands, activated with thiophosgene and subsequently linked to bovine serum albumin. The neoglycoproteins serve as immunoreagents to determine epitope specificities of monoclonal antibodies directed against highly immunogenic O-glycans located at the surface of Toxocara larvae. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00355-5