ChemicalBook CAS DataBase List alpha-D-ribofuranose,1,2-O-(1-methylethylidene)-

alpha-D-ribofuranose,1,2-O-(1-methylethylidene)- synthesis

14synthesis methods

Product Name:alpha-D-ribofuranose,1,2-O-(1-methylethylidene)-
CAS Number:37077-81-9
Molecular formula:C8H14O5
Molecular Weight:190.19

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alpha-D-ribofuranose,1,2-O-(1-methylethylidene)-

37077-81-9
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Yield: 79%

Reaction Conditions:

Stage #1:1,2-O-isopropylidene-α-D-allofuranose with sodium periodate in methanol;water at 0 - 20; for 3 h;
Stage #2: with sodium tetrahydroborate;ethanol at 0 - 20; for 16 h;

Steps:

Preparation of Compound 113.2
Compound 113.1 (6.2 g, 28.18 mmol, 1.00 eq) was dissolved in MeOH:H₂O (1:1, 20 V), then NaIO4 (12.1 g, 56.54 mmol, 2.00 eq) were added at 0°C. The mixture was stirred at rt for 3 hours. The mixture was evaporated to dryness. The residue (6.2 g, crude) was dissolved in EtOH (620 ml) and NaBH₄(2.5 g, 65.79 mmol, 2.00 eq) was added at 0°C. The mixture was stirred at rt for 16 hours. The residue was added to saturated NH4Cl aqueous (300 mL) at 0°C, the mixture was evaporated to dryness. The residue was purified by column chromatography over -192- silica gel (gradient elution: DCM/MEOH from 99:1 to 93:7). The fractions containing the product were collected and the solvent was evaporated to afford compound 113.2.79% yield (4.2 g, 22.11 mmol, 2 steps) white solid.1H NMR (400 MHz, Chloroform-d) d 5.81 (d, J = 3.8 Hz, 1H), 4.58 (t, J = 4.4 Hz, 1H), 4.00 (dd, J = 8.9, 5.1 Hz, 1H), 3.94 (dd, J = 12.3, 2.7 Hz, 1H), 3.85 (dt, J = 9.0, 3.2 Hz, 1H), 3.74 (dd, J = 12.3, 3.7 Hz, 1H), 1.57 (s, 3H), 1.37 ppm (s, 3H).13C NMR (101 MHz, CDCl3) d 112.78, 103.99, 80.64, 78.80, 70.85, 60.76, 53.45, 26.50 ppm

References:

JANSSEN PHARMACEUTICA NV;VERHOEVEN, Jonas;BRAMBILLA, Marta;CHINTA, Nagaraju;HULLAERT, Jan, Julien, A;JOUFFROY, Lucile, Marguerite;MEERPOEL, Lieven;NEOUCHY, Zeïna;THURING, Johannes, Wilhelmus, John, F;VERNIEST, Guido, Alfons, F;WINNE, Johan, Maurits WO2020/249663, 2020, A1 Location in patent:Page/Page column 191-192

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References

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References

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