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

HRID 51256

反応式

HRID 51256 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 883381,2-O-isopropylidene-alpha-D-xylofuranose収率 70.1%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86c0af43d04f425b9c521d471668ebcb
出典データセット
uspto-grants-2004_03
特許番号
US06713627B2

関連ノート

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