(2S,4S,5R,6R)-5-Acetylamino-4-(2,2-dimethyl-propionyloxy)-6-formyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 374604-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-5-Acetylamino-4-(2,2-dimethyl-propionyloxy)-6-formyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 374604-34-9
• 化学式: C₁₆H₂₅NO₈
• 分子量: 359.376
• InChiKey: GRLYMDNSBOSCRT-OVZMXSCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-5-Acetylamino-4-(2,2-dimethyl-propionyloxy)-6-formyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 Grubbs catalyst first generation 、 三氟甲磺酸 、 四氯化钛 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 生成 (2R,3R,4S,6S,2'R)-3-Acetylamino-4-(2,2-dimethyl-propionyloxy)-6-methoxy-3,4,5,6,3',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9
• 作为产物：
  描述：

  (2S,4S,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-(2,2-dimethyl-propionyloxy)-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium periodate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 (2S,4S,5R,6R)-5-Acetylamino-4-(2,2-dimethyl-propionyloxy)-6-formyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir

  摘要：

  We synthesized bicyclic ether sialidase inhibitors Such as tetrahydro-furan-2-yl. tetrahydro-pyran-2-yL and oxepan-2-yl derivatives related to zanamivir. These compounds substituted by diol at the C-3' and C-4' positions resulted in the retention of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. Compound I la in particular showed comparable efficacy in vivo relative to that of oseltamivir phosphate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01039-9