ChemicalBook CAS DataBase List L(+)-Gulonic acid gamma-lactone

L(+)-Gulonic acid gamma-lactone synthesis

5synthesis methods

Product Name:L(+)-Gulonic acid gamma-lactone
CAS Number:1128-23-0
Molecular formula:C6H10O6
Molecular Weight:178.14

L(+)-Gulonic acid gamma-lactone is a substrate for L-gulono-1,4-lactone oxidoreductase used in laboratory biosynthesis. It was prepared from L-ascorbic acid catalyzed by 5 % RU/AI2O3 for hydrogenation.

50-81-7 Synthesis

50-81-7
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1128-23-0
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Yield:1128-23-0 97%

Reaction Conditions:

with ruthenium on aluminium oxide;hydrogen;silica gel in water at 50; under 22502.3 - 30003 Torr; for 6 h;

Steps:

1 Example 1 : L-Gulonic acid gamma lactone
A solution of 23.1 g (0.13 mol) L-ascorbic acid and 0.1 g celite in 170.0 g water was hydrogenated over 3.0 g of 5 % RU/AI2O3 in a hydrogenator at 50 °C, 30-40 bar hydrogen pressure and stirred with 1300 rpm for 6 h. After steady uptake of hydrogen, the reaction was cooled down and the catalyst was removed by filtration over celite. Water was removed by lyophilisation to yield 22.66 g (97 %) of a white fluffy powder, which was pure by NMR. On recrystallization of the sample from water, crystalline material was obtained m.p.: 186.62 °C; [O]D^{1 9}: + 55° (c= 4, H2O); ¹H-NMR (400 MHz, DMSO-de): d = 3.44-3.55 (m, 2, -CH2); 3.71-3.77 (m, 1 , -CH); 4.16-4.24 (m, 2, -CH); 4.43-4.45 (q, 1 , -CH); 4.66 (t, 1 , -OH); 4.97-4.98(d, 1 , -OH); 5.33-5.34 (d, 1 , -OH); 5.78-5.80 (d, 1 , -OH).

References:

CLARIANT INTERNATIONAL LTD;BUDDE, Felix;MULLER, Thierry;HAUCK, Stefan WO2019/179773, 2019, A1 Location in patent:Page/Page column 14

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