Synthesis of 1-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)cytosine (F-ddC). A promising agent for the treatment of acquired immune deficiency syndrome

Okabe, Masami; Sun, Ruen-Chu; Zenchoff, Gladys B.

doi:10.1021/jo00014a013

Cited by 78 publications

(28 citation statements)

References 2 publications

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“…Thes ynthesis of dipeptide 5 (Scheme 3) started with alcohol 14,a ni ntermediate obtained starting from d-xylose according to ak nown procedure. [13] Alcohol 14 was transformed into the corresponding azide under Mitsunobu conditions.S aponification yielded acid 7,w hich was then coupled with trityl-protected l-histidine methyl ester to furnish dipeptide 15.S elective acetonide deprotection while retaining the trityl protecting group using 1n hydrogen chloride in acetic acid and careful work-up followed by double TBS protection and selective deprotection of the primary TBS group with HF·pyridine complex in THF or…”

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confidence: 99%

Total Synthesis and Structural Revision of the Antibiotic Tetrapeptide GE81112A

et al. 2018

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The total synthesis of the naturally occurring antibiotic GE81112A, a densely functionalized tetrapeptide, is reported. Comparison of spectral data with those of the natural product and the lack of biological activity of the synthesized compound led us to revise the published configuration of the 3-hydroxypipecolic acid moiety. This hypothesis was fully validated by the synthesis of the corresponding epimer.

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confidence: 99%

Total Synthesis and Structural Revision of the Antibiotic Tetrapeptide GE81112A

et al. 2018

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“…[13] Unter Mitsunobu-Bedingungen wurde 14 in das entsprechende Azid überführt und nach Verseifung die freie Carbonsäure 7 mit tritylgeschütztem l-Histidinmethylester umgesetzt. [13] Unter Mitsunobu-Bedingungen wurde 14 in das entsprechende Azid überführt und nach Verseifung die freie Carbonsäure 7 mit tritylgeschütztem l-Histidinmethylester umgesetzt.…”

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Totalsynthese und Strukturkorrektur des antibiotisch wirksamen Tetrapeptids GE81112A

et al. 2018

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Die erste Totalsynthese des antibiotischw irksamen Naturstoffs GE81112A, eines hoch funktionalisierten Tetrapeptids,w urdea bgeschlossen. Der Vergleichd er NMR-Daten und der biologischen Aktivitätd er synthetischen Verbindung mit den Daten fürd en Naturstoff führte zur Korrektur der publizierten absoluten Konfiguration eines stereogenen Zentrums der 3-Hydroxypipecolinsäure-Einheit und zur Synthese des biologischa ktiven GE81112A mit der korrekten Konfiguration.

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“…Ocabe et al . at Roche [43] also described another efficient procedure to prepare a similar sugar moiety (Scheme 17). …”

Section: Synthesis Of Carbohydrate Fluorinated Nucleosidesmentioning

confidence: 99%