methyl 5-O-allyl-2,3-O-isopropylidene-β-D-ribofuranoside | 114488-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-allyl-2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-(prop-2-enoxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 114488-50-5
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: KPFDYWBSJVBZSQ-GWOFURMSSA-N

物化性质

• 沸点：
  99-102 °C(Press: 0.2 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-O-allyl-2,3-O-isopropylidene-β-D-ribofuranoside 在 硫酸 、 水 、 四丁基碘化铵 、 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.25h， 生成 5-O-allyl 2,3,4-tri-O-benzyl-D-ribose diethyl dithioacetal
  参考文献：
  名称：

  Syntheses of oligomers of the capsular polysaccharide of the Haemophilus influenzae type b bacteria

  摘要：

  DOI：

  10.1016/s0040-4020(01)97590-8
• 作为产物：
  描述：

  卡培他滨杂质25 在 H-Dowex resin 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.0h， 生成 methyl 5-O-allyl-2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  Isopolar Phosphonate Analogue of Adenosine Diphosphate Ribose

  摘要：

  The synthesis of the bisphosphonate ADP-ribose, in which acetylene has replaced the oxygen of the pyrophosphate linkage, is reported.

  DOI：

  10.1021/ol0488993

文献信息

• Adhesin-oligosaccharide conjugate vaccine for Haemophilus influenzae
  申请人：AntexBiologics, Inc.

  公开号：US05843463A1

  公开（公告）日：1998-12-01

  Disclosed herein are immunogenic polysaccharide-H. influenzae adhesin protein conjugates, a purified H. influenzae adhesin protein and related proteins and polypeptides, DNA useful for producing the proteins, synthetic polyribosylribotol phosphate (PRP) oligosaccharides and intermediates useful for their synthesis, and methods of making and using these materials. The conjugates comprise a PRP fragment, preferably a synthetic oligosaccharide, coupled to an H. influenzae adhesin protein. The invention further comprises purified H. influenzae adhesin proteins and novel PRP oligosaccharides. The invention also comprises methods of producing these materials and using them in a vaccine to protect humans and other mammals against H. influenzae infection.

  本文披露了免疫原性多糖-H.流感嗜血杆菌粘附蛋白共轭物，纯化的H.流感嗜血杆菌粘附蛋白及相关蛋白和多肽，用于产生这些蛋白的DNA，用于合成的合成聚核糖核糖醇磷酸（PRP）寡糖和中间体，以及制备和使用这些材料的方法。这些共轭物包括一个PRP片段，优选是一个合成寡糖，与一个H.流感嗜血杆菌粘附蛋白偶联。该发明还包括纯化的H.流感嗜血杆菌粘附蛋白和新型PRP寡糖。该发明还包括制备这些材料并将其用于疫苗以保护人类和其他哺乳动物免受H.流感嗜血杆菌感染的方法。
• A metal-free route towards 1,5-disubstituted 1,2,3-triazolylmethylene linked disaccharides: Synthesis in a biodegradable hydroxyl-ammonium-based aqueous ionic liquid media
  作者：Anirban Kayet、Tanmaya Pathak

  DOI：10.1016/j.tetlet.2018.07.052

  日期：2018.8

  3-triazolylmethylene (1,5-DTM) linkers. The DTM linker was built by the 1,3-dipolar cycloaddition reactions of a series of sugar azides with vinyl sulfonylmethylene-modified furanose or pyranose under metal free conditions. Three different biodegradable hydroxylammonium based ionic liquids were studied in water as the reaction media. The N,N-dimethyl ethanolammonium formate-water mixture was found to

  使用1，5-二取代的1,2,3-三唑基亚甲基（1,5-DTM）接头将适当保护的碳水化合物连接在一起。DTM接头是通过一系列糖叠氮化物与乙烯基磺酰基亚甲基改性的呋喃糖或吡喃糖在无金属条件下的1,3-偶极环加成反应构建的。在水中作为反应介质，对三种不同的可生物降解的基于羟基铵的离子液体进行了研究。发现N，N-二甲基乙醇甲酸铵-水混合物是最好的反应介质，因为反应时间大大缩短以产生十几个新的1，5-DTM-连接的二糖。
• Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them
  申请人：Universidad de la Habana

  公开号：US06765091B1

  公开（公告）日：2004-07-20

  The present invention relates to the field of the Medicine, in particular with the chemical synthesis of oligosaccharide mixtures derived of ribose-ribitol-phosphate, which are used as active principle in vaccines for the prevention of infections caused by Haemophilus influenzae type b (Hib), as well as with the vaccines containing said oligosaccharide mixtures. The oligasaccharide mixtures obtained by chemical synthesis of the present invention, comprise repeating units of formulae (phosphate-ribosa-ribitol)n or (ribose-ribitol-phosphate)n of at least 5 compounds of structure A or B, which represent the repeating unit of the capsular polysaccharide of Haemophilus influenzae type b and differ only by n, being n a value contained between 4 and 25 (n≧4 y≦25), and wherein R1 or R2 is a spacer for conjugation to a carrier, with the condition of R1=spacer if R2=H, or R2=spacer if R1=H. The invention also is related with the immunogens containing such oligosaccharide mixtures, with the vaccines containing said immunogens and with the methods to prepare these oligosaccharides as mixtures. Furthermore, the invention includes the use of the vaccines, alone or combined with other vaccines, for the prevention of the infections caused by Haemophilus influenzae type b.

  本发明涉及医学领域，特别是关于核糖-核醇-磷酸酯类寡糖混合物的化学合成，这些混合物被用作预防由b型流感嗜血杆菌（Hib）引起的感染的疫苗的活性成分，以及含有这些寡糖混合物的疫苗。本发明的化学合成获得的寡糖混合物包括至少5种A或B结构的化合物的公式（磷酸酯-核糖-核醇）n或（核糖-核醇-磷酸酯）n的重复单元，这些化合物代表流感嗜血杆菌b型的胞囊多糖的重复单元，仅由n不同，其中n的值介于4和25之间（n≥4且≤25），其中R1或R2是用于与载体结合的间隔物，条件是如果R2=H，则R1=间隔物，如果R1=H，则R2=间隔物。该发明还涉及含有这种寡糖混合物的免疫原，含有该免疫原的疫苗以及制备这些寡糖混合物的方法。此外，该发明包括使用这些疫苗单独或与其他疫苗结合，用于预防由流感嗜血杆菌b型引起的感染。
• The synthesis of two repeating units of haemophilus influenzae type a capsular antigen
  作者：Barbara Grzeszczyk、Anna Banaszek、Aleksander Zamojski

  DOI：10.1016/0008-6215(88)84144-2

  日期：1988.5

  The repeating units 2-O-beta-D-glucopyranosyl-L-ribitol 4'- and 1-phosphate of Haemophilus influenzae type a capsular antigen have been synthesised by condensation of an alpha-D-glucopyranosyl bromide derivative with 5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol followed by selective deprotection of HO-4' or HO-1, phosphorylation, and removal of the blocking groups.

  流感嗜血杆菌型荚膜抗原的重复单元2-O-β-D-吡喃葡萄糖基-L-核糖醇4'-和1-磷酸酯是通过α-D-吡喃葡萄糖基溴化物衍生物与5-O-烯丙基缩合而合成的-1,2,3-三-O-苄基-D-核糖醇，然后对HO-4'或HO-1进行选择性脱保护，磷酸化并去除保护基。
• Synthesis of Glycoporphyrins by Cross-Metathesis Reactions
  作者：José Cavaleiro、Fernando de C. da Silva、Vitor Ferreira、Maria de Souza、Augusto Tomé、Maria Neves、Artur Silva

  DOI：10.1055/s-2008-1072718

  日期：2008.5

  An easy synthetic approach to glycoporphyrins from zinc(II)-2-vinyl-5,10,15,20-tetraphenylporphyrin or zinc(II)-protoporphyrin-IX dimethyl ester and O-allyl carbohydrate acetonides by cross-metathesis is reported.

  报告了一种通过交叉甲基化反应从锌(II)-2-乙烯基-5,10,15,20-四苯基卟啉或锌(II)-原卟啉-IX 二甲酯和 O-烯丙基碳水化合物丙酮合成糖卟啉的简便方法。