Dichloromethane → HCID 59226808, compound

HRID 659899Notes

Reaction equation

HRID 659899 reaction equation
[CH2:1]([O:8][CH:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]([CH2:42][O:43]CC2C=CC(OC)=CC=2)([CH2:31]OCC2C=CC(OC)=CC=2)[O:11][C:10]1([C:54]1[CH:59]=[CH:58][C:57]([F:60])=[C:56]([CH2:61]C2C=CC(OC3CCOC3)=CC=2)[CH:55]=1)[OH:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:74]1([O:80][CH3:81])[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1.F[C:83](F)(F)[C:84]([OH:86])=O.Cl[CH2:90]Cl>>[CH2:24]([O:23][C@H:13]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]2([C:54]3[CH:59]=[CH:58][C:57]([F:60])=[C:56]([CH2:61][C:77]4[CH:78]=[CH:79][C:74]([O:80][CH:81]5[CH2:83][CH2:84][O:86][CH2:90]5)=[CH:75][CH:76]=4)[CH:55]=3)[O:11][C:12]1([CH2:42][OH:43])[CH2:31][O:53]2)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86639769HCID 86639769, compound

Product 1

HCID 59226808HCID 59226808, compoundYield 83%

Procedure

To a solution of (4S,5S)-3,4,5-Tris-benzyloxy-2-{4-fluoro-3-[4-(tetrahydro-furan-3-yloxy)-benzyl]-phenyl}-6,6-bis-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-ol I-11i (275 mg, 0.28 mmol) in dichloromethane (2.0 mL) was added anisole (0.250 mL, 2.29 mmol) followed by a 20% solution of trifluoroacetic acid in dichloromethane (8.0 mL) at room temperature under nitrogen. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure. The crude residue was purified by flash chromatography over silica gel (eluting with a gradient of 10 to 30% ethyl acetate in heptane) to afford the product as a mixture of isomers (168 mg, 83% yield).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe crude residue was purified by flash chromatography over silica gel (
  3. washeluting with a gradient of 10 to 30% ethyl acetate in heptane)
  4. customto afford the product
  5. additionas a mixture of isomers (168 mg, 83% yield)

Sources & evidence

ORD record
ord-bc4d5109693143cf97fd52169e59a626
Source dataset
uspto-grants-2011_12
Patent number
US08080580B2

Reaction notes

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