Geminal hydroxy phosphonate derivatives of nucleusides: A novel class of nucleoside 5'-monophosphate analogues

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 955-958

  Králíková, Šárka ^a   Buděšínský, Miloš ^a   Masojídková, Milena ^a   Rosenberg, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0343415749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02107-3     Document Type: Article

References (22)

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18. Typical procedure for the preparation of compound 4b: Dimethylsulfoxide (0.213 ml, 3 mmol) was added with stirring to a solution of oxalyl chloride (0.131 ml, 1.5 mmol) in dichloromethane (3.5 ml) at -78°C under an argon atmosphere. After 10 min a solution of 3′-O-tert-butyldiphenylsilylthymidine (484 mg, 1 mmol) in dichloromethane (7 ml) was added dropwise and the reaction mixture was stirred for a further 30 min. Then the reaction was quenched by addition of triethylamine (0.7 ml, 5 mmol), the resulting suspension was stirred at low temperature for a further 5 min and, after allowing to warm to room temperature, dimethyl phosphite (0.183 ml, 2 mmol) was added. The reaction mixture was either set aside overnight at room temperature or heated at 40°C for several hours. The course of the reaction was checked by TLC on silica gel plates in chloroform:ethanol (9:1) and the product was detected both by UV monitoring and by spraying with 1% ethanolic solution of 4-(4-nitrobenzyl)pyridine [after a short heating and exposing to ammonia vapours the product (dimethyl ester) afforded an intense blue spot]. The reaction mixture was diluted with chloroform, extracted with water and dried over anhydrous sodium sulfate. Chromatography of the crude product on a silica gel column in chloroform-ethanol mixture afforded 459 mg (78%) of the expected 3′-O-tert-butyldiphenylsilyl-5′-C-dimethylphosphonothymidine (4a).
19. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185; Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
20. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185; Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
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