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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 473587Erstellt: 24. Oktober 2026

Ethyl chloroacetate → 5'-[(Carboethoxymethyl)methyamino]-5'-deoxy-8-methyladenosine

https://huagongshe.com/de/reaction/473587

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthyl chloroacetateHCID 7751—
EduktDiisopropylethylamineHCID 81531—
Edukt5'-Deoxy-5'-methylamino-8-methyladenosineHCID 25232717—
Edukt5'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-methyladenosineHCID 86649669—
LösungsmittelDimethylformamideHCID 6228—
Produkt5'-[(Carboethoxymethyl)methyamino]-5'-deoxy-8-methyladenosineHCID 25233251—

Reaktionsschritte

Compound 35 was prepared by the same procedure as described for the preparation of 6a using 4a (415 mg, 1.41 mm), ethyl chloroacetate (207 mg, 0.18 ml, 1.68 mm), DIEA (91 mg, 0.12 ml, 0.70 mm), and DMF (5 ml): yield 204 mg (38%), MS: m/z 381 (M+H)+; 1HNMR (DMSO-d6) δ 8.06 (s, 1H, H-2), 7.11 (bs, 2H, 6-NH2), 5.73 (d, 1H, H-1′, J1′,2′=5.4 Hz), 5.33 (bd, 1H, OH-2′, J2′-2′OH=4.7 Hz), 5.19 (bd, 1H, OH-3′, J3′-3′OH=4.9 Hz), 5.03 (ddd, 1H, H-2′, J1′,2′=5.4 Hz, J2′,3′=5.7 Hz, J2′-2′OH=4.7 Hz), 4.17 (ddd, 1H, H-3′, J2′,3′=5.7 Hz, J3′,4′=4.4 Hz, J3′-3′OH=4.9 Hz), 4.02 (q, 2H, CH3—CH2), 3.92-3.99 (m, 1H, H-4′), 3.27 (bs, 2H, NCH3—CH2), 2.83-2.90 (m, 1H, 5′-CH2), 2.70-2.79 (m, 1H, 5′-CH2), 2.53 (s, 3H, 8-CH3), 2.31 (s, 3H, N—CH3), 1.13 (t, 3H, OCH2—CH3); UV λmax, nm, pH 1, 258.9 (∈ 16,100), pH 7, 260 (∈ 15,900), pH 13, 260.1 (∈ 16,200).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08637485B2
Quelldatensatzuspto-grants-2014_01
ORD IDord-7119ee6e7c414467b7f98673e5d0d5ff
Quellennotizuspto-grants-2014_01