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

HRID 1818446Notes

Reaction equation

HRID 1818446 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8900HeptaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8c9cb2511abb4320ba6e82baf34bc839
Source dataset
uspto-grants-2009_10
Patent number
US07598373B2

Reaction notes

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