反応 #72435

反応方程式

Methyl 3-azido-2-O-benzyl-3-deoxy-D-glucopyranoside

Benzoyl chloride

Water

→

title compound

収率 78.0%

Methyl 3-azido-6-O-benzoyl-2-O-benzyl-3-deoxy-D-glucopyranoside

収率 78.0%

溶媒

pyridine

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at −20° C. for one hr
2. 2
   workup.STIRRINGthe mixture was stirred at −20° C. for 30 min
3. 3
   濃縮The contents were concentrated to dryness
4. 4
   workup.ADDITIONChloroform (10 mL) was added
5. 5
   洗浄the mixture was washed three times with 5 mL of a saturated aqueous sodium bicarbonate solution, three times with 5 mL of a 5% aqueous potassium bisulfate solution and three times with 5 mL of water
6. 6
   乾燥was dried over a Glauber's salt
7. 7
   濃縮was concentrated under the reduced pressure
8. 8
   その他The residue was purified by column chromatography on silica gel (25 g, hexane:ethyl acetate=3:1)

実験手順

Methyl 3-azido-2-O-benzyl-3-deoxy-D-glucopyranoside (93 mg) was dissolved in 0.84 mL of pyridine. Benzoyl chloride (45 μL) was added to the solution at −20° C. with stirring, and the mixture was stirred at −20° C. for one hr. Water (14 μL) was added thereto, and the mixture was stirred at −20° C. for 30 min. The contents were concentrated to dryness. Chloroform (10 mL) was added thereto, and the mixture was washed three times with 5 mL of a saturated aqueous sodium bicarbonate solution, three times with 5 mL of a 5% aqueous potassium bisulfate solution and three times with 5 mL of water, was dried over a Glauber's salt and was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (25 g, hexane:ethyl acetate=3:1) to give the title compound (97 mg, yield 78%).

出典