methyl 5-acetamido-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate | 117295-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate
• 英文别名: methyl 5-N-acetamido-3,5-dideoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate；methyl (2R,3R,4R,5R,6R)-5-acetamido-3-fluoro-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 117295-66-6
• 化学式: C₁₂H₂₀FNO₉
• 分子量: 341.291
• InChiKey: YZIZSFGTBAWUMK-DILALBHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.84
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  165.78
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate 生成 5-(Acetylamino)-3,5-Dideoxy-3-Fluoro-D-Erythro-Alpha-L-Manno-Non-2-Ulopyranosonic Acid
  参考文献：
  名称：

  NAKAJIMA, TATSUO;HORI, HIROSHI;OHRUI, HIROSHI;MEGURO, HIROSHI;IDO, TATSUO, AGR. AND BIOL. CHEM., 52,(1988) N 5, 1209-1215

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate 在 盐酸 、 Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以100%的产率得到methyl 5-acetamido-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate
  参考文献：
  名称：

  Synthetic study of 3-fluorinated sialic acid derivatives

  摘要：

  Sialic acid derivatives, analogs, and their conjugates are expected to be pharmaceutical candidates such as anti-influenza drugs and also useful probes for investigating the biological role of glycoconjugates. Derivatives of 3-fluorinated sialic acid (3-F-Sia) have been found to be excellent probes in investigating functions and mechanisms of a series of proteins. Here, we describe the syntheses of 3-F-Sia derivatives, which are useful in making biologically important conjugate probes. A practical method for the construction of 3-fluorinated sialosides based on the stereoselective formation of the corresponding anomeric O-trimethylsilyl ether and their nucleophilic attack by an alkyl halide, an allyl halide in particular, was developed. In addition, details of the synthesis of cytidine monophosphate (CMP)-3-F-Sia bearing a fluorescent tag, which has been proven to show dual functions as a substrate of CMP-sialic acid transporter (CST) and an inhibitor of sialyltransferase (STase), are described. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.12.010

文献信息

• [EN] COMPOUNDS FOR TREATING VIRAL INFECTIONS<br/>[FR] COMPOSÉS POUR TRAITER DES INFECTIONS VIRALES
  申请人：UNIV BATH

  公开号：WO2010029302A3

  公开（公告）日：2010-05-06
• SUDA, ISAO;OTAGUI, XIROSI;MEHGURO, XIROSI;IDO, TATSUO
  作者：SUDA, ISAO、OTAGUI, XIROSI、MEHGURO, XIROSI、IDO, TATSUO

  DOI：——

  日期：——