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Volumn 114, Issue 4, 1981, Pages 1234-1255

Nucleoside syntheses, XXII1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts

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EID: 84982068675     PISSN: 00092940     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/cber.19811140404     Document Type: Article
Times cited : (942)

References (84)
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    • Synthetische Verwendung von Epoxynitronen. I.N-(2,3-Epoxypropyliden)-cyclohexylamin-oxid, ein neues Reagens zur Synthese von ?-Methyliden-?-lactonen aus Olefinen
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    • Riediker, M.1    Graf, W.2
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    • who gives NMR data of the triflate salt of the corresponding cation derived from 1,2,3,4‐tera‐O‐acetyl‐β‐D‐ribofuranose
    • Tetrahedron Let. , vol.1977 , pp. 993
    • Stone1
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    • 19e, J. Org. Chem.
    • (1974)
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    • 4 for the synthesis of purine nucleosides compare.
  • 46
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    • Product Distribution in the Ribosylation Reactions of Adenine and 1-Deazapurine in the Presence of Stannic Chloride
    • 21c
    • (1976) HETEROCYCLES , vol.5 , pp. 285
    • Itosh, T.1    Mizuno, Y.2
  • 60
    • 84982504443 scopus 로고    scopus 로고
    • unpublishend. The composition of such a mixture varies. A Short reaction time and low tempreature during preparation of the O‐methyl‐2‐deoxyribose favors the kinetically controlled turanoside (28) whereas longer reaction times or failure to remove the last traces of acides after acylation withtuluoylchloride/pyridine leads gradually to increasing amounts of the undesired pyranosides 46.
    • Vorbrüggen, H.1    Bennua, B.2
  • 69
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    • N→N Alkyl and Glycosyl Migration of Purines and Pyrimidines. II. Glycosyl Migration of 3-Glycosyl-N6-acyladenine Derivatives
    • The same migration can be effected by hydrogen halide or mercury halides, 1446
    • (1970) CHEMICAL & PHARMACEUTICAL BULLETIN , vol.18 , pp. 732
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    • 3).
  • 82
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    • The discrepancies in the melting points should not be taken too seriously, since many nucleosides occur in several crystalline modifications. Compare for exaple the melting points of the benzoylated N‐1‐ and N‐3‐ribosides of 6‐methyluracil 23 and 24 for which we eventually obtained higher meltin crystals Another example is lumazine riboside 34b which also occurred in two crystalline modifications.


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