A New Synthetic Method of Nucleosides

Nishimura, Tomonori; Shimizu, Bunji; Iwai, Issei

doi:10.1248/cpb.11.1470

Cited by 63 publications

(14 citation statements)

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“…These problems were overcome by the Silyl-Hilbert-Johnson reaction. It was introduced by Birkofer [51,52], Nishimura [53,54], and Wittenburg [55]. The silylation with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) converts the rather polar often insoluble nucleobases into lipophilic compounds which are readily soluble in organic solvents.…”

Section: The Silyl-hilbert-johnson Reactionmentioning

confidence: 99%

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Seela¹,

Peng

2006

CTMC

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This review reports on the synthesis of 7-deazapurine ribonucleosides, including C-nucleosides, 2'-C-methyl derivatives and L-enantiomers. It covers the various aspects of convergent nucleoside synthesis such as the Schiff base procedure, the fusion reaction, the metal salt procedures, the Silyl-Hilbert-Johnson reaction, and the nucleobase anion glycosylation. The review discusses the scope and limitations of glycosylation reactions performed on 7-deazapurines. Peracylated ribose derivatives were now employed in the glycosylation, which overcome difficulties reported earlier.

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Section: The Silyl-hilbert-johnson Reactionmentioning

confidence: 99%

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Seela¹,

Peng

2006

CTMC

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“…The thiornethyl ether system is readily activated by iodine, allowing nucleophilic attack at the methylene position. As a result, compound 5 was coupled to purines and pyrimidines using the silylated base procedure (3, [17][18][19] to produce the desired compounds of general structure Z as outlined in Scheme 2.…”

Section: Discussion and Resultsmentioning

confidence: 99%

A trihydroxy acyclonucleoside series

Ogilvie¹,

Nguyen-Ba²,

Hamilton³

1984

Can. J. Chem.

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“…[38] Trimethylchlorosilane (6.51 g, 0.06 mole) and thymine (3.78g, 0.03 mole) were suspended in 100 mL dry benzene. The suspension was quickly stirred under N 2 and 8.25 mL triethylamine in benzene was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Antifreeze Protein‐Induced Selective Crystallization of a New Thermodynamically and Kinetically Less Preferred Molecular Crystal

Wang¹,

Wen²,

Golen³

et al. 2013

Chemistry A European J

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The formation of a new, dihydrate crystalline form of 5-methyluridine (m5U) was selectively induced by a protein additive, antifreeze protein (AFP) in a highly efficient manner (in 10−6 molar scale, while known kinetic additives need 0.1 molar scale). The hemihydrate form (form I, the only previously known crystalline form of m5U) and the dihydrate form of m5U (form II) obtained herein were characterized using X-ray crystallography and differential scanning calorimetry (DSC). Compared to form I, remarkably, form II is thermodynamically and kinetically less preferred. The presence of AFP can selectively inhibit the appearance of form I and hence allows the growth of form II, the pure form of which cannot grow directly from m5U supersaturated solutions under the same conditions. An explanation supported by both experimental and theoretical results was provided for the AFP-induced selection process. Implications on AFP-induced ice shape changes have also been discussed. Control of crystallization from supersaturated solutions is of great interest in both fundamental research and practical applications in fields like chemistry, pharmacology and materials science. These findings suggest that crystallization processes using AFPs is valuable for selective growth of hydrates and polymorphs of important pharmaceutical compounds.

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A New Synthetic Method of Nucleosides

Cited by 63 publications

References 0 publications

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

Progress in 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine - Ribonucleoside Synthesis

A trihydroxy acyclonucleoside series

Antifreeze Protein‐Induced Selective Crystallization of a New Thermodynamically and Kinetically Less Preferred Molecular Crystal

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