3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide | 849938-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide
• 英文别名: 3,4-Di-O-acetyl-2-O-benzyl-alpha-L-rhamnopyranosyl Bromide；[(2S,3S,4R,5R,6S)-4-acetyloxy-6-bromo-2-methyl-5-phenylmethoxyoxan-3-yl] acetate
• CAS: 849938-23-4
• 化学式: C₁₇H₂₁BrO₆
• 分子量: 401.254
• InChiKey: ZTIHEVNJXOLOAQ-MJQUHVBXSA-N

物化性质

• 沸点：
  442.8±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide 在 palladium dihydroxide 氢气 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3'',4''-二-O-乙酰基阿福豆苷
  参考文献：
  名称：

  Synthesis of a Potent and Selective Inhibitor of p90 Rsk

  摘要：

  The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

  DOI：

  10.1021/ol0500463
• 作为产物：
  描述：

  苯基3,4-二-O-乙酰基-alpha-O-苄基-1-硫代-alpha-L-吡喃鼠李糖苷 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide
  参考文献：
  名称：

  Synthesis of a Potent and Selective Inhibitor of p90 Rsk

  摘要：

  The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

  DOI：

  10.1021/ol0500463

文献信息

• Structural basis for the activity of the RSK-specific inhibitor, SL0101
  作者：Jeffrey A. Smith、David J. Maloney、Sidney M. Hecht、Deborah A. Lannigan

  DOI：10.1016/j.bmc.2007.03.087

  日期：2007.7

  reported the isolation, characterization, and synthesis of the natural product kaempferol 3-O-(3'',4''-di-O-acetyl-alpha-l-rhamnopyranoside), termed SL0101 [Smith, J. A.; Poteet-Smith, C. E.; Xu, Y.; Errington, T. M.; Hecht, S. M.; Lannigan, D. A. Cancer Res., 2005, 65, 1027-1034: Xu, Y.-M; Smith, J. A.; Lannigan, D. A.; Hecht, S. M. Bioorg. Med. Chem., 2006, 14, 3974-3977: Maloney, D. J.; Hecht, S. M.

  p90核糖体S6激酶（RSK）的不适当活性已与各种人类癌症以及其他病理相关。我们先前报道了称为SL0101的天然产物山奈酚3-O-（3''，4''-二-O-乙酰基-α-1-鼠李糖吡喃糖苷）的分离，表征和合成。CE，Poteet-Smith；徐Y TM Errington; Hecht，SM；Lannigan，DA Cancer Res。，2005，65，1027-1034：Xu，Y.-M。JA，史密斯；达兰·兰尼根（Lannigan）；Hecht，SM Bioorg。中 Chem。，2006，14，3974-3977：Maloney，DJ。Hecht，SM组织。Lett。，2005，7，1097-1099]。SL0101是一种有效且特异性的RSK抑制剂。因此，我们对这种先导化合物的抑制活性进行了结构基础分析。在体外激酶测定中，我们发现鼠李糖部分和4'，5的酰化作用 7-羟基负责维持RSK与
• Synthesis of Inhibitors of P90Rsk
  申请人：Hecht Sidney M.

  公开号：US20080269144A1

  公开（公告）日：2008-10-30

  The synthesis of the naturally occurring kaempferol glycoside SLO1O1-1, as well as analogs thereof, has been accomplished, as has its biochemical evaluation. SLO1O1-1 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthetic scheme of the invention verified the structural assignment of the natural SLO1O1-1 product and has provided access to material sufficient for detailed biological evaluation.

  自然存在的山柰酚苷SLO1O1-1及其类似物的合成已经完成，并对其进行了生化评估。SLO1O1-1在纳摩尔浓度下表现出选择性和强效的p90 Rsk抑制活性，而不抑制MEK、Raf或PKC等上游激酶的功能。本发明的合成方案验证了天然SLO1O1-1产物的结构分配，并提供了足够详细的生物评估材料。
• Synthesis of inhibitors of p90Rsk
  申请人：University of Virginia Patent Foundation

  公开号：US07605241B2

  公开（公告）日：2009-10-20

  The synthesis of the naturally occurring kaempferol glycoside SLO1O1-1, as well as analogs thereof, has been accomplished, as has its biochemical evaluation. SLO1O1-1 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthetic scheme of the invention verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

  天然存在的山柰酚苷SLO1O1-1及其类似物的合成已经完成，并进行了生化评估。SLO1O1-1在纳摩尔浓度下表现出选择性和强效的p90 Rsk抑制活性，而不抑制MEK、Raf或PKC等上游激酶的功能。该发明的合成方案验证了天然产物的结构分配，并提供了足够进行详细生物评估的材料。
• WO2006/86103
  申请人：——

  公开号：——

  公开（公告）日：——
• US7605241B2
  申请人：——

  公开号：US7605241B2

  公开（公告）日：2009-10-20