phenyl 3,4-di-O-acetyl-2-O-levulinoyl-1-thio-α-L-arabinopyranoside | 562834-43-9

• 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: phenyl 3,4-di-O-acetyl-2-O-levulinoyl-1-thio-α-L-arabinopyranoside
• 英文别名: [(2S,3R,4S,5S)-4,5-diacetyloxy-2-phenylsulfanyloxan-3-yl] 4-oxopentanoate
• CAS: 562834-43-9
• 化学式: C₂₀H₂₄O₈S
• 分子量: 424.472
• InChiKey: SQNVCEUNIVAWEE-FFGOWVMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2-O-levulinoyl-1-thio-α-L-arabinopyranoside 、 28-O-allyl-oleanate-3-yl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-trityl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以6%的产率得到28-O-allyl-oleanate-3-yl 3,4-di-O-acetyl-2-O-levulinoyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8
• 作为产物：
  描述：

  phenyl 3,4-O-isopropylidene-1-thio-α-L-arabinopyranoside 在 4-二甲氨基吡啶 、 Dowex-50 (H(+)) 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 phenyl 3,4-di-O-acetyl-2-O-levulinoyl-1-thio-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8