Trifluoroacetic acid → HCID 13336230, compound

HRID 1979524Notes

Reaction equation

HRID 1979524 reaction equation
[CH3:1][O:2][C@@H:3]1[C@@H:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([CH2:29][O:30]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:7][C@H:4]1[O:5][CH3:6].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C@@H:3]1[C@@H:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([CH2:29][OH:30])[O:7][C@H:4]1[O:5][CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13336188HCID 13336188, compound

Product 1

HCID 13336230HCID 13336230, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-O-methyl-3-O-octadecyl-5-O-trityl-β-D-xylofuranoside (3.2 g) in dry methylene chloride (32 ml) was added trifluoroacetic acid (3.2 ml) in one portion at ambient temperature. After stirring for 1.5 hours at the same temperature, the yellow solution was washed with water, aqueous sodium bicarbonate and water succesively, dried, and evaporated under reduced pressure. The residue was triturated in n-hexane to remove triphenylcarbinol by filtration. The filtrate was evaporated and then the residue was purified by column chromatography on silica gel (40 g, elution by chloroform) to yield 1.21 g of methyl 2-O-methyl-3-O-octadecyl-β-D-xylofuranoside as a thick oil.

Workup

  1. washthe yellow solution was washed with water, aqueous sodium bicarbonate and water succesively
  2. customdried
  3. customevaporated under reduced pressure
  4. customThe residue was triturated in n-hexane
  5. customto remove triphenylcarbinol
  6. filtrationby filtration
  7. customThe filtrate was evaporated
  8. customthe residue was purified by column chromatography on silica gel (40 g, elution by chloroform)

Sources & evidence

ORD record
ord-2f0a8d66337b4ba497182532ddd11643
Source dataset
uspto-grants-1984_11
Patent number
US04481196

Reaction notes

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