2,4:3,5-di-O-benzylidene-D-aldehydo-ribose | 107436-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,4:3,5-di-O-benzylidene-D-aldehydo-ribose
• 英文别名: (2R,4R,4aR,6R,8aR)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carbaldehyde
• CAS: 107436-58-8
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: FGRMUZCQGRXUEH-APAFKAMOSA-N

物化性质

• 沸点：
  490.7±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4:3,5-di-O-benzylidene-D-aldehydo-ribose 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 氨 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-pentitol-1-yl)nicotinamide
  参考文献：
  名称：

  Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside

  摘要：

  The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.

  DOI：

  10.1021/jm00388a030

文献信息

• Nucleosides. CXLVIII. : Synthesis of 6-(β-D-Ribofuranosyl)picolinamide. : A Novel C-Nucleoside from D-Ribonolactone
  作者：MAREK M. KABAT、KRZYSZTOF W. PANKIEWICZ、ELZBIETA SOCHACKA、KYOICHI A. WATANABE

  DOI：10.1248/cpb.36.634

  日期：1988.2.25

  2-bromopyridine (6) by mesylation of the 1'-hydroxyl group of 2 followed by treatment with trifluoroacetic acid. In a similar manner, the α-isomer 7 was prepared from 3. The same pyridine-C-nucleosides, 6 and 7, were also synthesized from the commercially available D-ribonolactone in seven steps.The bromo function of 2 and 3 was converted into the carboxamide group to give 6-(2, 4 : 3, 5-di-O-benz

  用2-溴-6-硫代吡啶处理2、4：3、5-二-O-亚苄基-D-醛-核糖（1），得到6-（2，4：3）的同分异构体和同分异构体的混合物，5-二-O-亚苄基-D-戊醇-1-基）-2-溴吡啶（分别为2和3）。对这些异构体进行色谱分离。通过2的1′-羟基的甲磺化，然后用三氟乙酸处理，将化合物2转化为6-（β-D-呋喃呋喃糖基）-2-溴吡啶（6）。用类似的方法，由3制备α-异构体7。七步也由市售D-核糖内酯合成了相同的吡啶-C-核苷6和7。将2和3的溴官能团转化进入羧酰胺基团，得到6-（2，4：3，5-二-O-亚苄基-D-戊糖醇-1-基）吡啶啉酰胺（10）及其同分异构体11。将10进行甲磺酸化，然后进行三氟乙酸处理，得到6-（β-D-呋喃呋喃糖基）吡啶甲酸酰胺（14）。对11的相似处理得到了α对应物15。
• Antiviral compounds. 1. Structure-activity relationship of some antiviral enediones derived from aldehydo sugars
  作者：Eli Breuer、David Melumad、Shalom Sarel、Eva Margalith、Ehud Katz

  DOI：10.1021/jm00355a007

  日期：1983.1

  A series of aldehydo sugars was subjected to condensation reactions with active methylene compounds. Acetylacetone was condensed with 2,4-O-benzylidene-3,5-O-dibenzoyl-D-ribose (1), 2,4:3,5-O-dibenzylidene-D-ribose (6), 2,3,4,5-tetraacetyl-D-ribose (7), and 2,3,4,5,6-pentaacetyl-D-glucose (9) to yield 3-ylidene-2,4-pentanedione derivatives 2, 11, 12, and 13, respectively. Sugar derivatives 1 and 6 were also condensed with benzoylacetone to give 14 and 18, with acetoacetanilide to give 16 and 19, with malononitrile to give 17 and 20, and with alpha-(gamma-butyrolactonylidene)triphenylphosphorane to give 21 and 22, respectively. Condensation of 1 with dibenzoylmethane gave 15. The double bond in compounds 2 and 11 was saturated by hydrogenation to give 23 and 24. All alpha, beta-unsaturated carbonyl compounds obtained exhibited antiviral activity and cytotoxicity. Compound 11 was found to have the most significant and selective antiviral activity against herpes simplex virus.
• Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside
  作者：Marek M. Kabat、Krzysztof W. Pankiewicz、Kyoichi A. Watanabe

  DOI：10.1021/jm00388a030

  日期：1987.5

  The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.