O-(3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->1)-(2S,3R)-2-azido-3-O-benzoyl-1,3-eicosanediol | 1334671-97-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: O-(3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->1)-(2S,3R)-2-azido-3-O-benzoyl-1,3-eicosanediol
• 英文别名: [(2R,3R,4R,5S,6S)-6-[(2S,3R)-2-azido-3-benzoyloxyicosoxy]-3,4-dibenzoyloxy-5-hydroxyoxan-2-yl]methyl benzoate
• CAS: 1334671-97-4
• 化学式: C₅₄H₆₇N₃O₁₁
• 分子量: 934.139
• InChiKey: TWKNZTNYAGGGBV-KAGVJCQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  68
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-benzyl-2-deoxy-3-O-p-methoxybenzyl-1-thio-2-trichloroacetamido-β-D-glucopyranoside 、 O-(3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->1)-(2S,3R)-2-azido-3-O-benzoyl-1,3-eicosanediol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以87%的产率得到O-(4,6-di-O-benzyl-2-deoxy-3-O-p-methoxybenzyl-2-trichloroacetamido-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->1)-(2S,3R)-2-azido-3-O-benzoyl-1,3-eicosanediol
  参考文献：
  名称：

  Synthesis of an O-sulfo LewisX analog as glycolipid antigen

  摘要：

  The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.027
• 作为产物：
  描述：

  (2S,3R,4E)-2-azido-3-O-benzoyl-4-eicosene-1,3-diol 在 N-碘代丁二酰亚胺 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 O-(3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->1)-(2S,3R)-2-azido-3-O-benzoyl-1,3-eicosanediol
  参考文献：
  名称：

  Synthesis of an O-sulfo LewisX analog as glycolipid antigen

  摘要：

  The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.027

文献信息

• Synthesis of an O-sulfo LewisX analog as glycolipid antigen
  作者：Shuhei Ueno、Shigeomi Horito

  DOI：10.1016/j.carres.2011.06.027

  日期：2011.10

  The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety. (C) 2011 Elsevier Ltd. All rights reserved.