Hydrazine hydrate (1:1) → 2-(2-Hydrazinocarbonylethylthio)ethyl beta-D-galactopyranoside

HRID 653330

Reaktionsgleichung

Reaktionsgleichung von HRID 653330
[O:1]([CH2:13][CH2:14][S:15][CH2:16][CH2:17][C:18]([O:20]C)=O)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].O.[NH2:23][NH2:24].C(Cl)(Cl)Cl.CO.O>C(O)C>[O:1]([CH2:13][CH2:14][S:15][CH2:16][CH2:17][C:18]([NH:23][NH2:24])=[O:20])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 21866399Chloroform methanol waterHCID 541048612-(2-Methoxycarbonylethylthio)ethyl beta-D-galactopyranoside

Produkt 1

HCID 544070492-(2-Hydrazinocarbonylethylthio)ethyl beta-D-galactopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(2-Methoxycarbonylethylthio)ethyl β-D-galactopyranoside (28) (500 mg) was dissolved in ethanol (99.5%; 2.5 ml) and hydrazine hydrate (85%; 1 ml) was added. The reaction mixture was left at room temperature over night (TLC; SiO2, chloroform/methanol/water 65:35:10, lower phase). Evaporation gave the title compound (29) as a syrup (pure by TLC and 1H-NMR) in quantitative yield. Recrystallization from ethanol gave the pure compound: mp 178°-179°; [α]D23 -2.2° (c 0.5; H2O); 1H-NMR (D2O, TMS as an external standard) δ 4.43 (d, 1H, J1,2 =7.7 Hz, H1), 4.07 (m, 1H, O--CH2 --CH2), 3.92-3.60 (m, 7H), 3.50 (dd, 1H, J2,3 =11.6 Hz, H2), 2.90, 2.86 (t, 2H each, J=7 Hz, --CH2S), 2.54 (t, 2H, CH2CO) 13C--NMR (D2O, TMS as an external standard) δ 176.1 (CO), 105.6 (C-1), 77.9, 75.4, 73.4, 71.6, 71.3 (C2-C6), 63.7 (O--CH2 --CH2), 36.5, 33.5, 29.9 (CH2S, CH2CO).

Aufarbeitung

  1. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-7ec7129c7d014f9186772227422fd256
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675392

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