3-(2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl)-1-propene → 3-(alpha-L-fucopyranosyl)-1-propene

HRID 1488284Notes

Reaction equation

HRID 1488284 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@H:8]([CH3:19])[O:7][C@H:6]1[CH2:20][CH:21]=[CH2:22])(=O)C.O(C)[Na]>CO>[C@@H:6]1([CH2:20][CH:21]=[CH2:22])[O:7][C@@H:8]([CH3:19])[C@@H:9]([OH:15])[C@@H:10]([OH:11])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 109799383-(2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl)-1-propeneHCID 178418582HCID 178418582, compound

Product 1

HCID 110741613-(alpha-L-fucopyranosyl)-1-propene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-propene (10.65 g, 33.9 mmol) in CH3OH (50 mL) was added NaOCH3 (183 mg, 3.4 mmol). After stirring at rt for 2 hr, the reaction mixture was neutralized with Amberlite IR120 (pre-washed with methanol 3×25 mL). The resin was filtered off and the filtrate was concentrated to give a white solid, which was recrystallized from EtOAc (˜200 mL) to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 1.22 (d, J=6.5, 3H), 2.41 (m, 1H), 2.47 (m, 1H), 3.73 (m, 2H), 3.85 (qd, J=6.5, 2.0, 1H), 3.90 (dd, J=8.9, 5.5, 1H), 3.99 (m, 1H), 5.07 (m, 1H), 5.15 (dq, J=17.2, 1.7, 1H), 5.85 (m, 1H).

Workup

  1. washthe reaction mixture was neutralized with Amberlite IR120 (pre-washed with methanol 3×25 mL)
  2. filtrationThe resin was filtered off
  3. concentrationthe filtrate was concentrated
  4. customto give a white solid, which
  5. customwas recrystallized from EtOAc (˜200 mL)

Sources & evidence

ORD record
ord-0af4d521a7c54692925c264df18267e3
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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