phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside | 849938-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside
• 英文别名: phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutan-2,3-diyl)-1-thio-α-L-rhamnopyranoside；(2R,3R,4aS,5S,7S,8R,8aR)-2,3-dimethoxy-2,3,5-trimethyl-8-phenylmethoxy-7-phenylsulfanyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine
• CAS: 849938-12-1
• 化学式: C₂₅H₃₂O₆S
• 分子量: 460.591
• InChiKey: JGCROGOYBCBYGT-XCRWYMFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以93%的产率得到苯基-alpha-O-苄基-1-硫代-alpha-L-吡喃鼠李糖苷
  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：

  phenyl 1-thio-α-L-rhamnopyranose 在 D(+)-10-樟脑磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 生成 phenyl 2-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside
  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

• 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。
• 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
• Synthesis of a Potent and Selective Inhibitor of p90 Rsk
  作者：David J. Maloney、Sidney M. Hecht

  DOI：10.1021/ol0500463

  日期：2005.3.1

  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.