Methanol → HCID 88089139, compound

A solution of ethanethiol (11.5 ml, 155 mmol) in 1N sodium methoxide in methanol (150 ml, 150 mmol sodium methoxide) was added to a solution of methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-ribofuranoside (50 g, 140 mmol in 200 ml dry methanol) and heated at reflux for 24 h. Solvents were removed by evaporation in vacuo, and the sticky residue was taken up in diethyl ether (300 ml) and washed with water (4×100 ml). The ether phase was dried and concentrated in vacuo to furnish a viscous oil. Fractional distillation (70° C. at 0.06 Torr) using a short-path distillation apparatus afforded 30.0 g (86.5% yield) of methyl 5-deoxy-5-ethylthio2,3-O-isopropylidene-β-D-ribofuranoside (III) as a colorless, viscous oil. TLC (silica; 25% ethylacetate in hexane): Rf 0.44 (III); visualization spray as in A above.

1. temperatureheated
2. temperatureat reflux for 24 h
3. customSolvents were removed by evaporation in vacuo
4. washwashed with water (4×100 ml)
5. dry with materialThe ether phase was dried
6. concentrationconcentrated in vacuo
7. customto furnish a viscous oil
8. distillationFractional distillation (70° C. at 0.06 Torr)

ORD record

ord-29e1fcd2151145ff82e007c3d9dcbf7c

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05366954