Toluene → HCID 68505031, compound

HRID 221935Notes

Reaction equation

HRID 221935 reaction equation
[CH2:1]([O:8][C@@H: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@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@@:10]21[C:51]1[S:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:52]Cl)[C:43]=1[CH2:42][CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:54]([C:56]1[CH:61]=[CH:60][C:59](B(O)O)=[CH:58][CH:57]=1)[CH3:55].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C@@H: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@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@@:10]21[C:51]1[S:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:52][C:59]3[CH:60]=[CH:61][C:56]([CH2:54][CH3:55])=[CH:57][CH:58]=3)[C:43]=1[CH2:42][CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 2734352Boronic acid, (4-ethylphenyl)-HCID 68508363HCID 68508363, compound

Product 1

HCID 68505031HCID 68505031, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Under a nitrogen stream, to a mixture of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-8-chloromethyl-3,3′,4,4′,5′,6′-hexahydro-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran] (41 mg, 0.05 mmol), 4-ethylphenylboronic acid (13.0 mg, 0.08 mmol), potassium phosphate (21.0 mg, 1.00 mmol), palladium acetate (1.2 mg, 0.005 mmol) and triphenylphosphine (2.6 mg, 0.01 mmol) was added toluene (2.6 mg, 0.5 mmol), and the resultant solution was stirred for 4 hours at 80° C. Solvent was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3)), to thereby obtain the titled compound (23 mg, 56%).

Workup

  1. concentrationSolvent was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:3))

Sources & evidence

ORD record
ord-29b5bffafd6940b997a4ad3a6fd5bc16
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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