alpha-D-Xylofuranose, 1,2:3,5-bis-O-(1-methylethylidene)- → 1,2-O-isopropylidene-alpha-D-xylofuranose

HRID 51256

반응식

HRID 51256 반응식
CC1(C)[O:7][C@@H:6]2[C@H:8]3[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@H:9]3[O:10][C@@H:5]2[CH2:4][O:3]1.O=C[C@@H]([C@H]([C@@H](CO)O)O)O>OS(O)(=O)=O>[CH3:14][C:12]1([CH3:15])[O:11][C@@H:9]2[C@@H:8]([C@@H:6]([OH:7])[C@@H:5]([CH2:4][OH:3])[O:10]2)[O:13]1

참가 물질

4

반응물 2

HCID 30337alpha-D-Xylofuranose, 1,2:3,5-bis-O-(1-methylethylidene)-HCID 644160aldehydo-D-Xylose

생성물 1

HCID 883381,2-O-isopropylidene-alpha-D-xylofuranose수율 70.1%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

1,2:3,5-Di-O-isopropylidene-D-xylofuranose (70.66 g, 0.30 mol) is treated with H2SO4 (0.1 M, 300 mL). Upon stirring, the xylose slowly dissolves. After 30 minutes, the reaction is quenched with NH4OH (pH 9.0) and half of the water removed at reduced pressure. The aqueous layer is diluted with brine (100 mL) and extracted with ethyl acetate (3×200 mL). A normal work-up provides an oil. Kugelrohr distillation provides 1,2-O-isopropylidene-D-xylofuranose (40 g, 68.5%); b.p. 120-135° C./0.4 mm Hg.

후처리

  1. customthe reaction is quenched with NH4OH (pH 9.0) and half of the water
  2. customremoved at reduced pressure
  3. additionThe aqueous layer is diluted with brine (100 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customA normal work-up provides an oil
  6. distillationKugelrohr distillation

출처 및 근거

ORD 기록
ord-86c0af43d04f425b9c521d471668ebcb
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713627B2

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