Triethylamine → (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1067044

Reaktionsgleichung

Reaktionsgleichung von HRID 1067044
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[C@@H]1[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=O)C.[CH2:49](N(CC)CC)C>C(Cl)Cl>[C:29]([O:28][C@@H:27]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:43][C@H:1]1[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:49])=[CH:5][CH:4]=1)(=[O:31])[CH3:30]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 90154-MethoxyphenolHCID 65367Trimethylsilyl triflateHCID 94752beta-D-Galactose pentaacetate

Produkt 1

HCID 13325756(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

p-methoxyphenol (20.5 mmol, 2.5 g) and trimethylsilyl trifluoromethanesulfonate (0.25 mL) were added to a solution of β-D-galactose pentaacetate (5.0 g, 12.8 mmol) in anhydrous CH2Cl2 at 0° C. under nitrogen. After 4 hours at 0° C., the reaction mixture was neutralized by addition of triethylamine (1 mL) and concentrated under reduced pressure. Purification by chromatography on silica gel (ethyl acetate-petroleum ether, v/v 1:3→1.5:1) afforded 6 as an amorphous white solid in 92% yield (5.35 g). Litt22 [αD]=+9.6° (c 0.54, CHCl3); [αD]23=+3° (c 1, CHCl3); 1H NMR (500 MHz, CDCl3): δ2.01, 2.06, 2.08 and 2.19 (4 s, 3H each, 4 OAc), 3.78 (s, 3H, OMe), 4.01 (m, 1H, H-5), 4.16 (dd, 1H, J5,6b 6.5 Hz, J6a,6b 11.3 Hz, H-6b), 4.23 (dd, 1H, J5,6a 6.9 Hz, H-6a), 4.92 (d, 1H, J1,2 8.0 Hz, H-1), 5.09 (dd, 1H, J2,3 10.4 Hz, J3,4 3.3 Hz, H-3), 5.5.44-5.48 (m, 2H, H-2 and H-4), 6.80 and 6.96 (2 d, 2H each, Ph).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customPurification by chromatography on silica gel (ethyl acetate-petroleum ether, v/v 1:3→1.5:1)

Quellen und Nachweise

ORD-Eintrag
ord-06111aa81d6847f4b8c961413b5d0bfa
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245902B1

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