Acetic Acid → HCID 131716689, compound

HRID 1073462Notes

Reaction equation

HRID 1073462 reaction equation
C([O:4][C:5]1([O:33][C@H:32]([CH2:34][O:35]C(=O)C)[C@@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:14]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([F:13])([F:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)C.[O-]CC.[Na+].C(O)(=O)C>C(O)C>[F:13][C:6]([F:12])([C:5]1([O:33][C@H:32]([CH2:34][OH:35])[C@@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:14]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[OH:4])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 131716687HCID 131716687, compound

Product 1

HCID 131716689HCID 131716689, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 1.83 g of 2-deoxy-2,2-difluoro-4,5-bis-O-(phenylmethyl)-D-arabino-3-heptulofuranosonic acid, ethyl ester diacetate in 5.1 ml of ethanol was added 3.4 ml of 1.5M sodium ethoxide in ethanol at 25° C. After 1.5 hours, the mixture was treated with 0.61 ml of glacial acetic acid and partitioned with ether and water. The organic layer was washed with water, sodium bicarbonate solution, and brine, dried and concentrated. The residue was subjected to column chromatography on silica gel to give an oil; CMR δ 100.1 (triplet, J=29.6 Hz, anomeric carbon)

Workup

  1. custompartitioned with ether and water
  2. washThe organic layer was washed with water, sodium bicarbonate solution, and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-3f99ed59321d4914a66de56a20b05c31
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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