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

HRID 40439

반응식

HRID 40439 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d72437301d8f450c8e58c63d57e0df84
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530177B2

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