CAS: 111549-97-4; (2S,3S,4R)-5-(Allyloxy)-2,3,4-Tris(Benzyloxy)Pentan-1-Ol

该化合物是一种受保护的脊椎醇衍生物,广泛用于碳水化合物化学和核核糖化合物合成,其主要优点包括存在Allyl和苯基保护群体,它们提供选择性的保护能力,使脊椎得以精确地发挥功能;所有基在温条件下提供正反向活动,而苯基群体则确保合成变异期间的稳定;该化合物是建造复合糖糖浆的多种多用途中间体,特别是在经修改的核素,核糖核酸和核糖合物的合成中.其明确界定的立体化学和保护群体战略使得在药和生物有机化学应用中进行受控制的渐进合成很有价值.

结构式图片

上下游产品

5-O-allyl-2,3,4-tri-O-benzyl-D-ribose benzyl bromide 5-O-allyl-2,3-di-O-benzyl-D-ribitol 5-O-allyl-2,3,4-tri-O-benzyl-1-O-trityl-D-ribitol 5-O-allyl-1-O-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 1-O-(2-O-Acetyl-3-O-allyl-5-O-benzyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol 5-O-Allyl-1-O-(3-O-allyl-2,5-di-O-benzoyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-D-ribitol 1-O-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-5-O-allyl-2,3,4-tri-O-benzyl-D-ribitol

合成工艺路线路线简述

    📜D-核糖置于盐酸,Sodium Tetrahydroborate,Busno23,Sodium Hydride,Calcium Carbonate,Mercury Dichloride体系中,用 甲醇,水,N,N-二甲基甲酰胺,甲苯,乙腈 用作溶剂,化学反应 20.5H,反应生成5-O-烯丙基-2,3,4-三-O-苄基-D-核糖醇
    参考文献:合成法测定肺炎链球菌c-多糖中核糖醇的构型
    标题:合成法测定肺炎链球菌c-多糖中核糖醇的构型
    摘要:C-多糖是所有已知肺炎链球菌血清型共有的抗原,是疫苗制备的潜在靶点.通过确定核糖醇的构型,解决了重复单元结构的最终不确定性,即含有两条磷酸胆碱侧链的五糖磷酸酯.通过合成两个以 D-或 L-核糖醇为中心的磷酸三糖片段,并将它们的 1H 和 13C NMR 光谱数据与天然多糖的光谱数据进行比较,从而进行构型分配.合成采用以不同顺序添加到不对称取代的手性核糖醇衍生物中的常见合成子,以获得核糖醇片段中相反的手性.含有 D-核糖醇的三糖的数据与天然材料的数据几乎相同,而含有 L-核糖醇的三糖的数据则有显着差异.特别是,两者之间的化学位移差异...
    Doi:10.1139/v99-056

    海关参考信息

    专利信息


    专利号:US-6765091-B1
    优先权日:1999-08-30
    标题:Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them
    发明人:BENCOMO VICENTE GUILLERMO VERE; ROY RENE
    权利人:UNIV LA HABANA; UNIV OTTAWA
    摘要: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. n 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 R 1 or R 2 is a spacer for conjugation to a carrier, with the condition of R 1 =spacer if R 2 =H, or R 2 =spacer if R 1 =H. n 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.

    专利号:CZ-2002721-A3
    优先权日:1999-08-30
    标题 :Mixtures of oligosaccharides, method of their synthesis and synthesis of disaccharide intermediate and disaccharide derivatives, immunogen, vaccine, macromolecule and use of disaccharides and macromolecules

    专利号:EP-0565590-B1
    优先权日:1990-12-21
    标 题:ADHESIN-OLIGOSACCHARIDE CONJUGATE VACCINE FOR $i(HAEMOPHILUS INFLUENZAE)
    发明人:KRIVAN HOWARD C; SAMUEL JAMES E; NORBERG NILS THOMAS
    权利人:ANTEX BIOLOG INC
    摘要: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.

    专利号:US-5843463-A
    优先权日:1990-12-21
    标题:Adhesin-oligosaccharide conjugate vaccine for Haemophilus influenzae
    发明人:KRIVAN HOWARD C; SAMUEL JAMES E
    权利人:ANTEXBIOLOGICS INC
    摘要: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.

    专利号:CN-119613465-A
    优先权日:2024-11-11
    标 题:Chemical synthesis method of haemophilus influenzae type b capsular polysaccharide derivative

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:Total Synthesis Of Lipoteichoic Acid OfStreptococcus Pneumoniae
    作者:Christian Marcus Pedersen,Ignacio Figueroa-Perez,Buko Lindner,Artur J. Ulmer,Ulrich Zähringer,Richard R. Schmidt |发布日期:2010.3.29
    摘要:Mixed Signals: The Glycophospholipid 1, Consisting Of Two Cholinylphospho‐galnac Units, Two 2‐acetamino‐4‐amino‐2,4,6‐trideoxygalactose Rings, Three Glucose Residues Each With Different Linkages To Other Sugar Units, And A Ribitolphosphate Residue, Has Been Synthesized. Target 1 Is Recognized By The Immune System, But Not By The Tlr‐2 Signaling Receptor As Previously Postulated.

    合成参考文献

    参考DOI号:10.1016/S0040-4039(01)81040-6
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