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2,4,6-Trimethylpyridine → 2-Bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside

HRID 653321
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 653321
Br[C@@:2]1([O:40][C@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[C@H:14]([O:15][CH:16]2[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]2[O:18][C:19](=[O:21])[CH3:20])[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:4]1[O:5][C:6](=[O:8])[CH3:7])O.CC1C=C(C)C=C(C)N=1.[Br:55][CH2:56][CH2:57][OH:58]>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[C:6]([O:5][C@@H:4]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:14]([O:15][C@H:16]2[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]2[O:18][C:19](=[O:21])[CH3:20])[C@@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[O:40][C@H:2]1[O:58][CH2:57][CH2:56][Br:55])(=[O:8])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 79532,4,6-TrimethylpyridineHCID 108982-BromoethanolHCID 543253951-bromo-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-D-galactopyranosyl)-alpha-D-galactopyranose

Produkt 1

HCID 228870902-Bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of the crude acetobromo sugar 49 (20.5 g; 29.3 mmol) in dry methylene chloride (100 ml) was added dropwise (ca 20 min) to a cold (-78°) solution of silver trifluoromethanesulfonate (nonpurified, commercial material; 10.3 g; 40 mmol), 2,4,6-tri-methylpyridine (3.6 g; 30 mmol) and 2-bromoethanol (17.5 g; 140 mmol) in methylene chloride (250 ml) under nitrogen. The reaction mixture was stirred in the dark for 23 h during which time it had reached room temperature. The yellowish-white precipitate, that had formed, was removed and the resulting colorless solution was washed consecutively with 1M hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water. Drying (sodium sulfate), filtration and evaporation gave a residue which crystallized spontaneously. Recrystallization from ethyl acetate, followed by evaporation of the mother liquor and recrystallization from methanol, gave a total of 16.6 g (77%) of the title compound 15. Melting point and optical rotation are shown in Table 1 and the 13C- and 1H-NMR data are shown in Table 2 and 3 , respectively.

Aufarbeitung

  1. customhad reached room temperature
  2. customThe yellowish-white precipitate, that had formed
  3. customwas removed
  4. washthe resulting colorless solution was washed consecutively with 1M hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water
  5. customDrying
  6. filtration(sodium sulfate), filtration and evaporation
  7. customgave a residue which
  8. customcrystallized spontaneously
  9. customRecrystallization from ethyl acetate
  10. customfollowed by evaporation of the mother liquor and recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-c091bbdad3ac476da739b5e4abfc978b
Quelldatensatz
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04675392

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