ChemicalBook CAS DataBase List Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside

Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside synthesis

9synthesis methods

Product Name:Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside
CAS Number:4099-85-8
Molecular formula:C9H16O5
Molecular Weight:204.22

67-56-1 Synthesis

67-56-1
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Methyl-2,3-O-isopropylidene-beta-D-ribofuranoside

4099-85-8
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Yield:4099-85-8 85%

Reaction Conditions:

with sulfuric acid at 5 - 20; for 0.416667 h;Inert atmosphere;Sonication;Time;

Steps:

Synthesis of methyl 2.3-O-isopropylidene-b-D-ribofuranoside (8)

A solution of D-ribose (700 mg, 4.663 mmol) in 5mL of dry acetone and5mL of dry methanol was prepared in a 125mL Erlenmeyer. The mixturewas stirred until the complete solubilization of the sugar. The flask wasthen placed in an ice bath, controlling the temperature under 5 C, whilethe atmosphere was kept dry with nitrogen gas. Subsequently, 0.5mL of98% H2SO4 was added dropwise and slowly, and the mixture was set intoan ultrasound bath. The reaction was allowed to proceed for different times(15, 20, 25, 30, 45, and 60 min). After completion of the reaction, solidNaHCO3 was added until the mixture reached pH 7. The mixture was vacuumfiltrated, and the solvent was evaporated under reduced pressure. Theresulting material was dissolved in 50mL of ethyl acetate and the organiclayer was washed with water (350 mL). The organic layer was dried withanhydrous Na2SO4, filtered, and concentrated under reduced pressure.Product 8 was obtained without further purification as yellow oil in an85% yield. IR (film, CHCl3) m (cm1): 3455.87 (OH), 2940.96 (CH),1457.94, 1378.88 (methyl isopropyl group). 1H NMR (CDCl3, 400.13 MHz):d 1.33 (s, 3H, CH3), 1.49 (s, 3H, CH3), 3.28 (d, 1H, J5,OH 8.5 Hz, OH),3.44 (s, 3H, OCH3), 3.60 (ddd, 1H, J 5a,5b 16.2 Hz and J5,4 3.0 Hz, H-5), 3.68-3.71 (m, 1H, H-5), 4.43 (t, 1H, J4,5 3.0 Hz, H-4), 4.59 (d, 1H,J3,2 5.9 Hz, H-3), 4.83 (d, 1H, J2,3 5.9 Hz, H-2), 4.98 (s, 1H, H-1).13NMR (CDCl3, 100.61 MHz): d 24.86 (CH3), 26.51 (CH3), 55.66 (OCH3),64.15 (C-5), 81.64 (C-2), 85.96 (C-3), 88.49 (C-4), 110.13 (C-1), 112.29 (C-7). The data are in agreement with that in the literature.[30]

References:

Evangelista, Tereza Cristina Santos;Aquino, Gabriel Alves Souto de;Donza, Marcio Roberto H.;Leit?o, Rafael Lisboa;Carvalho, Victor Salarolli de;Kaiser, Carlos Roland;Ferreira, Sabrina Baptista [Journal of Carbohydrate Chemistry,2021,vol. 40,# 5,p. 243 - 268]

50-69-1 Synthesis