allyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside | 154779-68-7

• 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 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 154779-68-7
• 化学式: C₄₆H₄₆O₁₅
• 分子量: 838.862
• InChiKey: XMZYRNMEOLVVRG-JAJGRRLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  61.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  180.81
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 、 phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS 4 Angstroem 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以85%的产率得到allyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

  摘要：

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00053-3
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-2-(((2R,3S,4R,5R,6R)-6-(allyloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 camphor-10-sulfonic acid 作用下， 反应 4.0h， 生成 allyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  A facile and regioselective synthesis of partially benzoylated 3',4'-O-isopropylidene-β-lactosides as standardized key intermediates for sialyl Lewis X (sLex) analogues

  摘要：

  DOI：

  10.1016/0008-6215(93)84013-v