CAS: 7355-55-7; 2-Amino-3,7-Dihydropyrrolo[2,3-D]Pyrimidin-4-One

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7-Deaza-2'-脱氧鸟苷置于盐酸体系中,用 水 作为反应溶剂,化学反应生成 2-氨基-4-羟基吡咯并[2,3-D]嘧啶
参考文献:8-Aza-7-脱氮鸟嘌呤和相关的吡唑并[3,4-D]嘧啶的2'-脱氧核糖呋喃糖苷的合成
标题:8-Aza-7-脱氮鸟嘌呤和相关的吡唑并[3,4-D]嘧啶的2'-脱氧核糖呋喃糖苷的合成
摘要:所述ñ(1)-和ñ(2)-(2'-Deoxyribofuranosides)1和2,分别为8-氮杂-7-脱氮鸟嘌呤的制备通过相转移的糖基化在存在或不存在卜4 Nhso 4作为6-氨基-4-甲氧基-1 H-吡唑并[3,4-D]嘧啶(7C)与2-脱氧-3,5-二-O-(对甲苯甲酰基)-α-D-赤型-的催化剂戊呋喃糖酰氯(10).以类似的方式,但是没有催化剂并且使用thf作为有机相,6-氨基-4-氯核苷11B和12B从7A合成并分别转化为n(1)-和n(2)-取代的4-Thioxo类似物17A和18A.的比率ñ(1)-至ñ(2)-Glycosylation为2:1 7C和1:1为图7A,即 取决于核碱基的结构.与n(1)化合物相比,N(2)-(β-D-2'-脱氧核糖呋喃糖苷)的h +催化n-糖基水解速率大大降低.但是,N(1)-核苷1它是2'-脱氧鸟苷的等排物,具有足够的稳定性,可稍后用于固相寡核苷酸合成.
DOI:10.1002/hlca.19860690714

专利信息

专利号:US-6639059-B1
优先权日:1999-03-24
标 题 :Synthesis of [2.2.1]bicyclo nucleosides
发明人：KOCHKINE ALEXEI; FENSHOLDT JEF; PFUNDHELLER HENRIK M
权利人:EXIQON AS
摘要:A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. From compounds of the general formula II, such as 3-O-aryl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose, intermediates of the general formula III are suitable for coupling with silylated nucleobases. Upon one-pot base-induced ring-closure and desulfonation of the formed [2.2.1]bicyclo nucleoside, a short route to each the LNA (Locked Nucleic Acid) derivatives of adenosine, cytosine, uridine, thymidine and guanidine is demonstrated. The use of the 5'-sulfonated ring-closed intermediate also allows for synthesis of 5'-amino- and thio-LNAs.

专利号:US-6005097-A
优先权日:1996-06-14
标题 :Processes for high-yield diastereoselective synthesis of dideoxynucleosides
发明人：CHEN SHU-HUI; LI XIUYAN
权利人:VION PHARMACEUTICALS INC
摘要:The present invention relates to methods for substantially enhancing the stereoselective synthesis of β-anomeric nucleoside analogs. In methods according to the present invention, the introduction of a phenylseleno group onto a blocked lactone sugar precursor may be selected so that the desirable phenylseleno substituent is introduced on the side of the blocked lactone away from the blocking group. This stereospecific introduction of the phenylseleno group in sugar precursor allows the synthesis of nucleoside analogs and in particular, 2',3',-dideoxy- and 2',3'-dideoxy-2',3'-didehydronucleoside analogs in very high yield. In certain preferred embodiments, the preferred phenylseleno blocked lactone is obtained in an amount representing approximately 90% or more of the total amount of the stereoisomers obtained. In even more preferred embodiments, the amount of the preferred stereoisomer is at least 95%, even more preferably at least about 97% of the total amount of phenylseleno blocked lactone produced.

专利号:US-6069250-A
优先权日:1995-12-14
标 题 :Method and compositions for the synthesis of dioxolane nucleosides with β-configuration
发明人：MANSOUR TAREK; CIMPOIA ALEX; BEDNARSKI KRZYSZTOF
权利人:IAF BIOCHEM INT
摘要:The present invention relates to methods and compositions for preparing biologically important nucleoside analogues containing 1,3-dioxolane sugar rings. In particular, this invention relates to the stereoselective synthesis of the beta (cis) isomer by glycosylating the base with an intermediate of formula (II) below a temperature of about -10 DEG C. wherein R1 and L are as defined herein.

专利号:EP-1501848-B1
优先权日:2002-05-08
标 题 :Synthesis of locked nucleic acid derivatives
发明人：SORENSEN MADS DETLEF; WENGEL JESPER; KOCH TROELS; CHRISTENSEN SIGNE M; ROSENBOHM CHRISTOPH; PEDERSEN DANIEL SEJER
权利人:SANTARIS PHARMA AS
摘要:The invention relates to a novel strategy for the synthesis of Locked Nucleic Acid derivatives, such as alpha-L-oxy-LNA, amino-LNA, alpha-L-amino-LNA, thio-LNA, alpha-L-thio-LNA, seleno-LNA and methylene LNA, which provides scalable high yielding reactions utilising intermediates that also can produce other LNA analogues such as oxy-LNA. Also, the compounds of the formula X are important intermediates that may be reacted with varieties of nucleophiles leading to a wide variety of LNA analogues. (Formula I)

专利号:US-2010304368-A1
优先权日:2006-09-20
标 题:Components and method for enzymatic synthesis of nucleic acids
发明人：CHERKASOV DMITRY; BAEUML ENGLEBERT; BAEUML ELISABETH
权利人:CHERKASOV DMITRY; BAEUML ENGLEBERT; BAEUML ELISABETH
摘要:Novel methods for enzymatic synthesis of nucleic acid chains and the substrates for the same are disclosed. The methods are based on a step-wise enzymatic reaction. The sequencing of nucleic acids is an example of the use of the claimed methods.

专利号:US-7897758-B2
优先权日:2005-04-27
标题 :Activators for oligonucleotide and phosphoramidite synthesis
发明人：WOLTER ANDREAS; LEUCK MICHAEL
权利人:SIGMA ALDRICH CO
摘要:The present invention discloses novel methods for the synthesis of oligonucleotides and nucleoside phosphoramidites. The methods are based on employing aryl-substituted 5-phenyl-1H-tetrazoles with perfluoroalkyl groups on the aromatic ring as activators. In one aspect the novel activators are used in the synthesis of oligonucleotides via the phosphoramidite approach. In this aspect the activators are highly efficient and can be applied with very short coupling times. In a further aspect, the activators of the invention are used in the synthesis of phosphoramidites through the reaction of nucleosides comprising a free hydroxyl group with phosphitylating agents. In this aspect the activators provide very pure phosphoramidites under mild conditions. The activators of the invention are further characterized by being highly soluble, non-hygroscopic and non-hazardous.