5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose | 136035-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose
• 英文别名: 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-L-ribo-hexofuranose；[(1S)-1-[(2R,3R)-3-(1,3-dioxoisoindol-2-yl)-5-hydroxyoxolan-2-yl]ethyl] acetate
• CAS: 136035-06-8
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: GSHHHINFYBTYMR-WCBFBDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.14
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-2,3,6-trideoxy-3-phthalimido-β-L-ribo-hexofuranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(5-O-acetyl-3-phthalimido-2,3,6-trideoxy-α-L-ribo-hexofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Evaluation of Antiviral Activity of L-Acosamine and L-Ristosamine Nucleosides of Furanose Configuration.

  摘要：

  Mercuric-catalyzed hydrolysis of acetylated L-rhamnal 1 gives an alpha,beta-unsaturated aldehyde 2. 1,4-Addition of DBU-phthalimide salt with concomitant acetyl shift resulted in L-ribo and L-arabino isomers of 5-O-acetyl-2,3,6-trideoxy-3-phthalimido-hexofuranose 3 and 4. After acetylation at the anomeric center, coupling with silylated thymine resulted in three new nucleosides, with L-acosamine and L-ristosamine of furanose configuration as the carbohydrate moiety. The target compounds have been evaluated for their antiviral activity against HIV and HSV-1.

  DOI：

  10.3891/acta.chem.scand.45-0616
• 作为产物：
  描述：

  Acetic acid (E)-(S)-1-((R)-1-hydroxy-ethyl)-4-oxo-but-2-enyl ester 以30%的产率得到
  参考文献：
  名称：

  LAU, JESPER;PEDERSEN, ERIK B.;NIELSEN, CARSTEN M., ACTA CHEM. SCAND., 45,(1991) N, C. 616-620

  摘要：

  DOI：

文献信息

• 2,3,6-Trideoxy-5-<i>O</i>-(4-nitrobenzoyl)-3-trifluoroacetamido-L-<i>ribo</i>-hexofuranosyl Bromide - A Suitable Furanoid Ristosamine Glycosylation Reagent
  作者：Krzysztof Walczak、Jesper Lau、Erik B. Pedersen

  DOI：10.1055/s-1993-25943

  日期：——

  5-O-Acetyl-2,3,6-trideoxy-3-phthalimido-ß-L-ribo-hexofuranose (2) was converted to its corresponding methyl glycoside 3. After deprotection with 33% methylamine in ethanol and subsequent protection of the amino group with trifluoroacetic anhydride and the hydroxy group with 4-nitrobenzoyl chloride, the resulting compound 5 was transformed into the appropriate glycosyl bromide 7 via the 1-O-acetyl derivative 6. Compound 7 was coupled with daunomycinone in the presence of yellow mercury(II) oxide and mercury(II) bromide.

  5-O-乙酰基-2,3,6-三脱氧-3-邻苯二甲酰亚胺基-β-L-核糖-呋喃己糖 (2) 转化为其相应的甲基糖苷 3。用 33% 甲胺的乙醇溶液脱保护并随后保护用三氟乙酸酐去除氨基，用4-硝基苯甲酰氯去除羟基，所得化合物5通过1-O-乙酰基衍生物6转化为合适的糖基溴7。化合物7在黄汞存在下与道诺霉素偶联( II)氧化物和溴化汞(II)。