alpha-D-Ribofuranose, 1,3,5-tribenzoate → [(2R,3R,4R,5R)-3,5-Bis(benzoyloxy)-4-fluorooxolan-2-yl]methyl benzoate

HRID 1365575Notes

Reaction equation

HRID 1365575 reaction equation
[C:1]([O:9][C@H:10]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:13]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:11]1O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(F)([F:48])C1C=CC=C(C)C=1)CC)C>C(#N)C>[C:1]([O:9][C@H:10]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:13]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:11]1[F:48])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11005061alpha-D-Ribofuranose, 1,3,5-tribenzoateHCID 11820531N,N-Diethyl-alpha,alpha-difluoro-3-methylbenzylamine

Product 1

HCID 66808794[(2R,3R,4R,5R)-3,5-Bis(benzoyloxy)-4-fluorooxolan-2-yl]methyl benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
200 °C

Procedure

Into a pressure resistant vessel (200 ml) of the closed type which was made of Teflon and attached with a fiber optic temperature sensor, a stirrer rod, α-D-ribofuranose 1,3,5-tribenzoate (11 mmole; 5.1 g) and 50 ml of acetonitrile were placed. To the resultant mixture, N,N-diethyl-α,α-difluoro(3-methyl)benzylamine (23.2 mmole; 49.5 g) was slowly added under a nitrogen atmosphere. The temperature was then raised to 200° C. at a rate of 20° C./min under stirring, and the reaction was allowed to proceed for 20 minutes. After the reaction was completed, the reaction product was poured into 200 ml of ice water, and the organic layer was separated. The aqueous layer was treated by extraction with 50 ml of acetonitrile. The obtained two organic layers were combined, washed with pure water, dried with magnesium sulfate and then filtered. The obtained organic solution was concentrated using an evaporator, and the concentrated solution was analyzed in accordance with the liquid chromatography. As the result, 2.8 g (the yield: 55%) of 2-deoxy-2-fluoro-α-D-ribofuranose 1,3,5-tribenzoate of the object compound was obtained.

Workup

  1. customthe organic layer was separated
  2. additionThe aqueous layer was treated by extraction with 50 ml of acetonitrile
  3. customThe obtained two organic layers
  4. washwashed with pure water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe obtained organic solution was concentrated
  8. customan evaporator

Sources & evidence

ORD record
ord-ac798f23e7a04e53a4da20f591eec64d
Source dataset
uspto-grants-2011_02
Patent number
US07892518B2

Reaction notes

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