Boron trifluoride etherate → 1-O-trichloroethyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronic acid methyl ester

HRID 40439ノート

反応式

HRID 40439 の反応式
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12](=[O:35])[C@H:13]1[O:22][C@@H:17](OC(=O)C)[C@H:16]([O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:27][C:28](=[O:30])[CH3:29])[C@@H:14]1[O:31][C:32](=[O:34])[CH3:33].[Cl:36][C:37]([Cl:41])([Cl:40])[CH2:38][OH:39]>ClCCl>[CH3:10][O:11][C:12](=[O:35])[C@H:13]1[O:22][C@H:17]([O:39][CH2:38][C:37]([Cl:41])([Cl:40])[Cl:36])[C@H:16]([O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:27][C:28](=[O:30])[CH3:29])[C@@H:14]1[O:31][C:32](=[O:34])[CH3:33]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 8259TrichloroethanolHCID 95087Methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate

生成物 1

HCID 666170921-O-trichloroethyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BF3-Et2O (15 ml) was added dropwise to a cooled solution at 0° C. of 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid methyl ester (11.23 g, 0.03 mol) and 2,2,2-trichloroethanol (20 ml) in anhydrous dichloromethane (250 ml) under inert atmosphere. The mixture was stirred at room temperature overnight and then washed with 1N HCl (100 ml), water (100 ml) and brine (100 ml). The organic phase was dried over sodium sulphate, filtered and concentrated to dryness. 1-O-trichloroethyl-2,3,4-tri-O-acetyl-α-D-glucopyranuronic acid methyl ester 1 (8.95 g) was obtained after recrystallization of the crude product from ether.

後処理

  1. washwashed with 1N HCl (100 ml), water (100 ml) and brine (100 ml)
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-d72437301d8f450c8e58c63d57e0df84
出典データセット
uspto-grants-2013_09
特許番号
US08530177B2

反応ノート

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