2,3,5-tri-O-benzoyl-α-D-ribofuranose | 79439-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzoyl-α-D-ribofuranose
• 英文别名: [(2R,3R,4R,5S)-3,4-dibenzoyloxy-5-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 79439-67-1
• 化学式: C₂₆H₂₂O₈
• 分子量: 462.456
• InChiKey: VJYJDSXEIXFNRI-BILGYAHESA-N

物化性质

• 沸点：
  619.8±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-D-ribofuranose 在 silica gel 作用下， 生成 1,3,5-三苯甲酰基-D-呋喃核糖
  参考文献：
  名称：

  1,2-反式呋喃呋喃糖基叠氮化物合成中立体选择性的起源研究

  摘要：

  发现1,2-反式，路易斯酸催化过酰化呋喃糖酶的叠氮化物的立体选择性取决于叠氮化物供体的反应性（叠氮化物亲核性）和相对于相邻的2-O-酰基在异头中心的构型。团体。由SnCl4和Me3SiN3生成的1,2-反式糖基酯与高度亲核的叠氮化物供体的反应具有立体特异性。根据叠氮化物物种与双环1，2-酰基氧鎓（1,2-O-烷基鎓二基-D-呋喃呋喃糖）离子的快速反应来解释结果，该双环离子是主要形成的反应性中间体。当使用1，2-顺式糖基酯作为起始原料时，选择性降低（90-94％de）。如果使用较少亲核性的Me3SiN3与Me3SiOTf催化剂结合使用，则对1,2-反式对应物也是如此。出现这种情况是由于出现了反应性较高但选择性较低的氧碳鎓（糖呋喃诺酮）离子，在前一种情况下作为主要形成的反应性中间体，或者在后一种情况下与酰基氧鎓离子平衡后出现。具有核糖基，木糖基和3-脱氧-赤-戊基构型的受保护的1，2-反式β-

  DOI：

  10.1016/s0008-6215(99)00293-1
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3,5-tri-O-benzoyl-α-D-ribofuranose
  参考文献：
  名称：

  Structure and Total Synthesis of HF-7, a Neuroactive Glyconucleoside Disulfate from the Funnel-Web Spider Hololena curta

  摘要：

  Spider venom toxins have attracted considerable attention for their ability to block the action of excitatory amino acids such as glutamate and aspartate. A new neuroactive compound designated HF-7 was isolated in 1993 from the venom of a funnel-web spider, Hololena curta. HF-7 was shown to block kainate receptors and, albeit weakly, L-type calcium channels. Spectroscopic analysis established the structure of HF-7 as an unusual acetylated, disulfated fucopyranosyl guanosine, with the acetate ester attached at the 4-position of an alpha-linked fucose ring and two sulfates attached to the ribose ring. Because insufficient quantities of natural HF-7 were available for chemical degradation or X-ray diffraction analysis, total synthesis of three candidate structures was used to establish the identity of HF-7. Once HF-7 was fully characterized as 3'-O-(4 "-O-acetyl-alpha-L-fucopyranosyl)gnanosine-2',5-dusulfate, an improved, targeted synthesis of the natural product was developed.

  DOI：

  10.1021/ja990274q

文献信息

• ENZYME DETECTION/ASSAY METHOD AND SUBSTRATES
  申请人：——

  公开号：US20010019823A1

  公开（公告）日：2001-09-06

  The invention relates to a method of detecting and/or assaying nucleoside hydrolases or nucleoside phosphorylases using a chromogenic substrate. Preferred chromogenic substrates have formula (I) where X is OH, or H, and Y is the residue of Y—OH where Y—OH is a chromophore or a compound readily converted to a chromophore and the substrates are hydrolysed by the nucleoside hydrolase to yield ribose or 2-deoxyribose plus Y—OH. Alternatively those substrates may be phosphorylysed by nucleoside phosphorylase to yield ribose-1-phosphate plus Y—OH. The methods may be used to detect and/or assay parasites in biological samples.

  该发明涉及一种使用显色底物检测和/或测定核苷水解酶或核苷酸磷酸酶的方法。首选的显色底物具有式(I)，其中X为OH或H，Y为Y—OH的残基，其中Y—OH为色团或易于转化为色团的化合物，这些底物通过核苷水解酶水解产生核糖或2-脱氧核糖以及Y—OH。或者这些底物可能被核苷酸磷酸酶磷酸化产生核糖-1-磷酸加Y—OH。这些方法可用于检测和/或测定生物样本中的寄生虫。
• Process for the preparation of 2'-halo-beta-L-arabinofuranosyl nucleosides
  申请人：——

  公开号：US20030060622A1

  公开（公告）日：2003-03-27

  The present invention is directed to the process for the preparation of 2′-deoxy-2′-halo-&bgr;-L-arabinofuranosyl nucleosides, and in particular, 2′-deoxy-2′-fluoro-&bgr;-L-arabinofuranosyl thymine (L-FMAU), from L-arabinose, which is commercially available and less expensive than L-ribose or L-xylose, in ten steps. All of the reagents and starting materials are inexpensive and no special equipment is required to carry out the reactions.

  本发明涉及制备2'-脱氧-2'-卤代-β-L-阿拉伯呋喃核苷的过程，特别是从商业可获得且价格较低的L-阿拉伯糖制备2'-脱氧-2'-氟-β-L-阿拉伯呋喃胸苷（L-FMAU），共经过十个步骤。所有试剂和起始原料都廉价，并且不需要特殊设备来进行反应。
• SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150152131A1

  公开（公告）日：2015-06-04

  A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

  下列的化合物，其化学式为[1D]（其中R1A、R1B、R2A、R2B、R3A和R3B代表氢原子、可选择取代的C1-6烷基等），可作为生产硫代核苷的中间体，本发明的生产方法可作为一种生产硫代核苷的方法。
• Process for the production of peracylated 1-0-glycosides
  申请人：Schering AG

  公开号：US20030069402A1

  公开（公告）日：2003-04-10

  The invention relates to a process for the production of peracylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar is a monosaccharide that is functionalized in 1-OH-position, R represents methyl, ethyl, propyl, isopropyl, tbutyl, phenyl, n means 2, 3 or 4, X means —COO— or —NH—and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of peracylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  该发明涉及一种生产通式I的过酰化1-O-糖苷或其盐的工艺，其中糖是在1-OH位置上被官能化的单糖，R代表甲基、乙基、丙基、异丙基、叔丁基、苯基，n取2、3或4，X代表—COO—或—NH—，L代表一条直链、分支、饱和或不饱和的C1-C30碳链，该碳链可以被基团中断或取代。根据该发明的工艺从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产具有1-O官能化侧链的过酰化糖苷。
• Enzyme detection/assay method and substrates
  申请人：——

  公开号：US20020132263A1

  公开（公告）日：2002-09-19

  The invention relates to a method of detecting and/or assaying nucleoside hydrolases or nucleoside phosphorylases using a chromogenic substrate. Preferred chromogenic substrates have formula (I) where X is OH, or H, and Y is the residue of Y—OH where Y—OH is a chromophore or a compound readily converted to a chromophore and the substrates are hydrolysed by the nucleoside hydrolase to yield ribose or 2-deoxyribose plus Y—OH. Alternatively those substrates may be phosphorylysed by nucleoside phosphorylase to yield ribose-1-phosphate plus Y—OH. The methods may be used to detect and/or assay parasites in biological samples. 1

  本发明涉及使用显色底物检测和/或测定核苷酸酶或核苷酸磷酸酶的方法。首选显色底物具有公式（I），其中X是OH或H，Y是Y-OH残基，其中Y-OH是一种色团或易于转化为色团的化合物，底物通过核苷酸酶水解产生核糖或2-去氧核糖加上Y-OH。或者，这些底物可被核苷酸磷酸酶磷酸化，形成核糖1-磷酸加上Y-OH。该方法可用于检测和/或测定生物样品中的寄生虫。