Tetrabutylammonium Fluoride → HCID 59065928, Verbindung

HRID 25739

Reaktionsgleichung

Reaktionsgleichung von HRID 25739
[Si]([O:8][C@H:9]1[C@@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:23]2=[O:38])[O:11][CH:10]1[C@H:39]([OH:71])[C@@H:40]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[NH:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:63])[C@H:47]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH:48][C:49](=[O:58])[O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@H:9]1[C@@H:13]([OH:14])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:23]2=[O:38])[O:11][CH:10]1[C@H:39]([OH:71])[C@@H:40]([C:64]([O:66][C:67]([CH3:68])([CH3:70])[CH3:69])=[O:65])[NH:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:63])[C@H:47]([CH2:59][CH:60]([CH3:61])[CH3:62])[NH:48][C:49](=[O:58])[O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 86587940tert-butyl (5S,12S)-12-[(R)-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy) methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Produkt 1

HCID 59065928HCID 59065928, VerbindungAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

By using an analogous procedure to that described for Example 44, tert-butyl (5S,12S)-12-[(R)-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (100 mg, 0.097 mmol, obtained from Example 4) and tetrabutylammonium fluoride 0.292 ml, 0.292 mmol) were stirred in tetrahydrofuran (1 ml) under nitrogen for 2.5 hours at room temperature. The residue was chromatographed (flash column, silica gel, 6.5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-12-[(R)-[(3S,4R,5R)-3,4-dihydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (55 mg, 71%) as a white solid.

Aufarbeitung

  1. customThe residue was chromatographed (flash column, silica gel, 6.5% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-f896a48434c048e7be615bc13de91e05
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858591B2

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