Methanol → methyl 3,4-dideoxy-3-methyl-alpha-D-glycero-hex-3-enopyranos-2-ulose

0.1 ml of concentrated sulfuric acid was added to 30 ml of a dry methanol solution containing 500 mg of 1,6-anhydro-3,4-dideoxy-3-methyl-β-D-glycero-hex-3-enopyranos-2-ulose (Intermediate No. 2), and the mixture was stirred at room temperature for 48 hours. Then, 30 ml of a saturated sodium hydrogencarbonate aqueous solution was added thereto, and the mixture was stirred at room temperature for 15 minutes and then concentrated under reduced pressure. Then, 200 ml of ethyl acetate was added thereto, and the mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=2:3) to obtain 350 mg of the desired compound (Intermediate No. 20) as a colorless liquid. The NMR analytical data of this product are as follows. 1H NMR(CDCl3,400 MHz): 1.86(3H,m); 1.95(1H,t,J=6.0Hz); 3.54(3H,s); 3.76(1H,ddd,J=11.2,6.8,6.0Hz); 3.84(1H,ddd,J=11.2,6.0,3.6Hz); 4.63(1H,m); 4.80(1H,s); 6.68(1H,m)

1. stirringthe mixture was stirred at room temperature for 15 minutes
2. concentrationconcentrated under reduced pressure
3. additionThen, 200 ml of ethyl acetate was added
4. washthe mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=2:3)

ORD-Eintrag

ord-e27bdab2483248f3a033b0fa710ac16c

Quelldatensatz

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05380834