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HRID 399098Erstellt: 24. Oktober 2026

4-Methoxybenzaldehyde → 3-Benzyl-6-benzyloxymethyl-1-(4-methoxybenzyl)-(3S, 6S)-perhydro-2,5-pyrazinedione

https://huagongshe.com/de/reaction/399098

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt4-MethoxybenzaldehydeHCID 31244—
EduktL-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 90234—
EduktFmoc-phenylalanineHCID 978331—
EduktHOAt DICHCID 131720865—
Produkt3-Benzyl-6-benzyloxymethyl-1-(4-methoxybenzyl)-(3S, 6S)-perhydro-2,5-pyrazinedioneHCID 57303670—

Reaktionsschritte

TentaGel resin was coupled with FmocPhe (Mitsunobu conditions) and reductively alkylated with anisaldehyde. BocSer(OBzl) was coupled with HOAt/DIC and after Boc-deprotection the DKP formed in 4% TEA/toluene (12 h). Yield: 7.1 mg (8.3%). 1H-NMR (400 MHz, CDCl3): δ=1.60 (dd, J=6.4, 6.4 Hz, 1 H), 3.22 (dd, J=3.4, 10.0 Hz, 1 H), 3.28 (dd, J=2.8, 10.0 Hz, 1 H), 3.44 (dd, J=2.2, 6.4 Hz, 1 H), 3.81 (s, 3 H), 3.85 (d, J=14.6 Hz, 1 H), 4.07 (dd, J=2.2, 6.4 Hz, 1 H), 4.18 (dd, J=2.8 3.4 Hz, 1 H), 4.21 (d, J=8.0 Hz, 1 H), 4.25 (d, J=8.0 Hz, 1 H), 5.54 (d, J=14.6 Hz, 1 H), 6.42 (broad s, 1 H), 6.87-6.89 (m, 2 H), 7.19-7.40 (m, 12 H). 13C-NMR (101 MHz, CDCl3): δ=36.6, 46.5, 55.8, 59.0, 72.1, 73.5, 114.6, 126.9, 127.8, 128.0, 128.2, 128.7, 129.1, 130.2, 130.5, 135.2, 137.4, 159.8, 163.5, 166.7. Anal. Calcd. for C27H28 N2O4.2H2O: C, 67.48; H, 6.71; N, 5.83, found: C, 68.00; H, 6.18; N, 5.65.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05817751
Quelldatensatzuspto-grants-1998_10
ORD IDord-6b794abab66644579aebc93e57d90aa2
Quellennotizuspto-grants-1998_10