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    • 1. 发明授权
    • Chiral disulfonimides
    • 手性二磺酰亚胺
    • US09079869B2
    • 2015-07-14
    • US13203382
    • 2010-03-02
    • Benjamin ListFrank LayPilar Garcia Garcia
    • Benjamin ListFrank LayPilar Garcia Garcia
    • A61K31/554C07D285/36C07D285/01
    • C07D285/01
    • Chiral disulfonimides having the formula I to III, wherein at least one of the groups A and B in the compound of formula I, C and D of the compound in formula II, and E and F of the compound in formula III is a chiral group, or E and F together form a chiral backbone, X is C, Si, O, N or S, and n is 0, 1, 2, 3, 4, 5 or 6, where n is >1 only if X is C, and G is as defined herein, and to the organic salts, metal salts and metal complexes thereof, are suited as NMR shift reagents and as reagents for racemate splitting, and also as chiral Brønsted acid catalysts or chiral Lewis acid catalysts for activating ketones, aldehydes and alkenes, and also as catalysts in the organic synthesis.
    • 具有式I至III的手性二磺酰亚胺,其中式I化合物中的基团A和B中至少一个,式II化合物中的C和D,以及式III中化合物的E和F是手性基团 ,或E和F一起形成手性主链,X为C,Si,O,N或S,n为0,1,2,3,4,5或6,其中只有X为C时,n为> 1 和G如本文所定义,并且其有机盐,金属盐和金属络合物适合用作NMR位移试剂和用作外消旋体分裂的试剂,以及用作活化酮的手性布朗斯台德酸催化剂或手性路易斯酸催化剂, 醛和烯烃,以及有机合成中的催化剂。
    • 2. 发明申请
    • SULFUR TRANSFER REAGENTS FOR OLIGONUCLEOTIDE SYNTHESIS
    • 用于寡核苷酸合成的硫转移试剂
    • US20090306358A1
    • 2009-12-10
    • US12134136
    • 2008-06-05
    • Andrei P. Guzaev
    • Andrei P. Guzaev
    • C07H1/00C07D285/01
    • C07D285/08C07D417/12C07H21/00
    • The use of N-formamidino-5-amino-3H-1,2,4-dithiazole-3-thiones as novel, efficient sulfur-transfer reagents is disclosed. The sulfur transfer from these reagents to compounds containing P(III) atom, triphenylphosphine, 5′-O-DMT-thymidine 2-cyanoethyl-(N,N-diisopropyl)phosphoramidite, and 5′-O-DMT-3′-O-levulinyl dithymidilyl 2-cyanoethyl phosphite, was studied in solution by 31P NMR and HPLC. The sulfur transfer from title compounds was also studied in the solid-phase synthesis of oligonucleotide phosphorothioates by phosphoramidite methods. In this application, the efficiency of the sulfur transfer reaction for 2′-deoxyoligonucleotides was better than 99.5%. The novel sulfurizing agents are synthesized, at low cost, using simple chemical methods. As opposed to many sulfur transfer reagents known in the prior art such as 1,2-benzodithiol-3-one-1,1-dioxide (Beaucage reagent) and 5-ethoxy-3H-1,2,4-dithiazole-2-one (EDIT), the sulfurizing agents disclosed herein are highly stable in solution, which increases their practical and commercial value.
    • 公开了N-甲酰胺基-5-氨基-3H-1,2,4-二噻唑-3-硫杂的新型高效硫转移试剂的应用。 从这些试剂向含有P(III)原子,三苯基膦,5'-O-DMT-胸苷2-氰基乙基 - (N,N-二异丙基)亚磷酰胺和5'-O-DMT-3'-O 通过31 P NMR和HPLC在溶液中研究了亚磷酸二乙酰基二缩水甘油基2-氰乙基亚磷酸酯。 还通过亚磷酰胺方法在寡核苷酸硫代磷酸酯的固相合成中研究了标题化合物的硫转移。 在本申请中,2'-脱氧核糖核苷酸的硫转移反应的效率优于99.5%。 以低成本,简单的化学方法合成了新型硫化剂。 与现有技术中已知的许多硫转移试剂相反,例如1,2-苯并二硫醇-3-酮-1,1-二氧化物(Beaucage试剂)和5-乙氧基-3H-1,2,4-二噻唑-2-酮 一种(EDIT),本文公开的硫化剂在溶液中高度稳定,这增加了它们的实用和商业价值。