2-氨基-6-氟-9-(4-羟基-3-羟甲基丁基)嘌呤的合成

报道了2-氨基-6-氟-9-(4-羟基-3-羟甲基丁基)嘌呤(1)的合成, 通过对起始原料2-氨基-6-氯-9-(4-乙酰氧基-3-乙酰氧甲基丁基)嘌呤(2)水解脱去乙酰基, 得到2-氨基-6-氯-9-(4-羟基-3-羟甲基丁基)嘌呤(3). 化合物3与三甲胺乙醇溶液在混合溶剂[V(THF)∶V(DMF)＝3∶1]中反应得到相应的氯化铵盐4, 然后与KF在DMF溶剂中反应, 得到化合物1. 产品经UV-vis, IR, ¹H NMR, ¹⁹F NMR和MS表征. 考察了反应温度、氟化试剂等因素对氟化反应的影响, 为6位含氟的嘌呤核苷类化合物的合成提供了一种直接、简易的新方法.     

Synthesis of 3-(6-alkylaminopurin-9-yl)-2,3-dideoxy-D-thero-pentopyranoses and their reduction to 3-(6-alkylaminopurin-9-yl)-2,3-dideoxy-D-thero-pentitols

3-(6-Alkylaminopurin-9-yl)-2,3-dideoxy-D-threo-pentopyranoses 3 were prepared by condensation of unprotected 2-deoxy-D-ribose (2) with N⁶-alkyladenines 1 in a phosphorus pentoxide reagent mixture. Reduction of the pentoses 3 gave the corresponding 3-(6-alkylaminopurin-9-yl)-2,3-dideoxy-D-threo-pentitols 4. The structures of 3 and 4 were determined by ¹³C nmr, ¹H nmr and 2D ¹H nmr (COSY).     

Synthesis of 2′,3′-dideoxynucleosides via C-S bond cleavage: N-glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycoside

N-Glycosylation of 2,3-dideoxy-1-[(2-pyridylmethyl)thio]glycosides (1a) using several activators is described. NBS-promoted glycosylation reaction utilizing either the α- or β-thiodideoxyglycoside proceeded smoothly at −78 °C to give the corresponding dideoxynucleoside in a β-selective manner, presumably through a common glycosyl donor.     

Practical enantiospecific syntheses of (+) erythro-9- (2s-hydroxy-3r-nonyl) adenine.

Three enantiospecific syntheses of 1S (2S-benzyloxethyl) oxirane (9) from L-ascorbic acid, L(+) tartaric acid, and Z-butene 1,4-diol are reported. The conversion of 9 to 2S-hydroxy-3R-nonylamine (19) is also described.     

Synthesis of 3-O-aryl esters of (R,S)-9-(2,3-dihydoxypropyl)adenine and its pyrimidine analogs as new potential inhibitors ofS-adenosyl-L-homocysteine hydrolase

With the aim of searching for new antiviral agents of the acyclonucleoside type, 3-O-arly esters of (R,S)-9-(2,3-dihydroxypropyl)adenine adenine and its pyrimidine analogs have been synthesized. Alkylation of adenine and cytosine by aryl glycidyl ethers in the presence of potassium carbonate affords 46–76% yields of the corresponding N⁹- and N¹-substituted derivatives. The interaction of aryl glycidyl ethers with trimethylsilyl derivatives of uracil and thymine also results in 41–57% yields of N¹-monosubstituted products with identical acyclic chain structure.Scientific-Research Institute of Pharmacology at the Volgograd Medical Academy, Volgograd 400066, Russia.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 82–86, January, 1999.     

5－O－苯甲酰基－2，3－二脱氧－3－硝基－D－呋喃戊糖甲苷的合成研究

５－Ｏ－苯甲酰基－２，３－二脱氧－３－硝基－Ｄ－呋喃戊糖甲苷的合成研究史达清，周龙虎，高原，戴桂元（徐州师范学院化学系，徐州，２２１００９）关键词呋喃戊糖苷，Ｄ－木糖，异构化，合成５－Ｏ－苯甲酰基－２，３－二脱氧－３－硝基－Ｄ呋喃戊糖甲苷１是合成河豚...     

Enantiomeric forms of 9-(5,6-dideoxy-α-d-arabino-hex-5-enofuranosyl)adenine and preparation of 9-(6-deoxy-β-d-galactofuranosyl)adenine: Further results with the acetolysis of hexofuranosides

Acetolysis of methyl 5,6-dideoxy-2,3-0-isopropylidene-β-d-ribo-hex-5-enofuranoside (1) and condensation of the product with 6-benzamidochloromercuripurine by the TiCl₄ method, gave 9-(5,6-dideoxy-α-d-arabino-hex-5-enofuranosyl) adenine (3) in low yield after removal of blocking groups. The main product was the D ribo nucleoside which was selectively destroyed by periodate oxidation to facilitate chromatographic purification of 3. The enantiomer 6 was prepared from methyl 5,6-dideoxy-2,3-0-isopropylidene-β-l-ribo-hex-5-enofuranoside (5) by the exact same route. The acetolysis reaction, in contrast to most previous experience, failed to epimerize C-2 of the sugar completely. An improved preparation of 6 is described which started from D-galactose. In addition, the latter pathway was used to prepare 9-(6-deoxy-β-d-galactofuranosyl)adenine (17).     

2-[(9-苯基)-9H-3-咔唑基]-5-[(9-对甲苯基)-9H-3-咔唑基]吡啶的合成及其光谱性能

以咔唑和2,5-二溴吡啶为初始原料,经Ullmann反应、NBS亲电取代反应和Suzuki偶联等反应,合成了一种新型的磷光配体2-[(9-苯基)-9H-3-咔唑基]-5-[(9-对甲苯基)-9H-3-咔唑基]吡啶(5),其结构经1HNMR,ESI-MS及元素分析表征。研究了5在二氯甲烷中的荧光光谱和紫外吸收光谱。     

Analogs of purine nucleosides. 4. 7-Alkylated 9-(2-hydeoxymethyl)guanine

7,9-Disubstituted guaninium hydrohalides were synthesized by the reaction of 9- and 7-(2-hydroxymethyl)guanines with alkyl halides. The effect of the structure of the alkylating agent on the direction and yield of the alkylation reaction was established. The possibility of the conversion of the salts obtained to the free bases in a weakly alkaline medium was investigated. The synthesized compounds were characterized by the UV and ¹H and ¹³C NMR spectra. The ability of the synthesized compounds to inhibit replication of the herpes virus (VPG-1) was demonstrated.See [1] for Communication 3.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 641–646, May, 1989.