(2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-(2,2-difluoro-but-3-enyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 374604-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-(2,2-difluoro-but-3-enyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-2,2-difluorobut-3-enoxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2-methoxyoxane-2-carboxylate
• CAS: 374604-56-5
• 化学式: C₂₆H₄₅F₂NO₉Si
• 分子量: 581.727
• InChiKey: LZCKSAZNKCQGMV-MSBIWLHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-(2,2-difluoro-but-3-enyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 Lindlar's catalyst 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四氧化锇 、 Grubbs catalyst first generation 、 sodium azide 、 Dowex 50W (H⁺) 、 硫酸 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三氟乙酸 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,2'R,3'R,4'S)-3-Acetylamino-5',5'-difluoro-4-guanidino-3',4'-dihydroxy-3,4,3',4',5',6'-hexahydro-2H,2'H-[2,2']bipyranyl-6-carboxylic acid
  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：

  Methyl-5-(acetylamino)-4-O-(tert-butyldimethylsilyl)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester 、 toluene-4-sulfonic acid 2-(2,2-diethyl[1,3]dioxolan-4-yl)ethyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S,5S,6R)-5-Acetylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-(2,2-difluoro-but-3-enyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-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

文献信息

• Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir
  作者：Takeshi Masuda、Satoshi Shibuya、Masami Arai、Shuku Yoshida、Takanori Tomozawa、Akiko Ohno、Makoto Yamashita、Takeshi Honda

  DOI：10.1016/s0960-894x(02)01039-9

  日期：2003.2

  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.