D-Ribofuranose → 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose

HRID 1818446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818446
OC1O[C@H](CO)[C@@H](O)[C@H]1O.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20]([O:28][C@:29]1([CH3:54])[C@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@H:33]([CH2:44][O:45][C:46](=[O:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[O:32][CH:30]1[OH:31])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.COC(C)(C)C>CN(C1C=CN=CC=1)C.COCCOC.O.CCCCCCC>[C:11]([O:31][C@@H:30]1[O:32][C@H:33]([CH2:44][O:45][C:46](=[O:53])[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@@:29]1([CH3:54])[O:28][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

9

Edukt 4

HCID 5779D-RibofuranoseHCID 7412Benzoyl chlorideHCID 15413tert-Butyl methyl etherHCID 573769702,3,5-Tri-O-benzoyl-2-C-methyl-D-ribofuranose

Produkt 1

HCID 108755601,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranoseAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

The protective group at C-1 of the ribofuranose is made in the immediately preceding step. Benzoyl chloride is added to a 5° C. solution of 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribofuranose in approximately a 2:1 molar ratio, along with DMAP and TEA in anhydrous DME. The reaction is stirred and allowed to run overnight, after which it is quenched with ice water and aqueous sodium carbonate solution. THF is then removed, and the mixture is extracted with ethyl acetate. Washing, drying and solvent removal produces a thick, oily product. The latter has added to it tert-butyl methyl ether, heptane and water, and is stirred for approximately 2 hours at about 20° C. The final product, 1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose, is obtained in 52% yield and greater than 98% purity, after washing and vacuum drying (see FIG. 1, compound 4, Scheme 1).

Aufarbeitung

  1. customafter which it is quenched with ice water and aqueous sodium carbonate solution
  2. customTHF is then removed
  3. extractionthe mixture is extracted with ethyl acetate
  4. washWashing
  5. customdrying
  6. customsolvent removal
  7. customproduces a thick, oily product
  8. stirringis stirred for approximately 2 hours at about 20° C

Quellen und Nachweise

ORD-Eintrag
ord-8c9cb2511abb4320ba6e82baf34bc839
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598373B2

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