Potassium Carbonate → (3'r,4's,5s,5's,6'r)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3',4',5',6'-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]

HRID 221920Notes

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:47]1[CH:46]=[C:45]3[C:48](I)=[CH:49][S:50][C:44]3=[CH:43][C:42]=1[CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Ag]=O.[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[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:47]1[CH:46]=[C:45]3[C:48]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([CH2:48][CH3:49])=[CH:44][CH:43]=4)=[CH:49][S:50][C:44]3=[CH:43][C:42]=1[CH2:41][O:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-iodo-3′,4′,5′,6′-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7H),2′-[2H]pyran] (0.05 g, 0.061 mmol), potassium carbonate (25.5 mg, 0.184 mmol), silver oxide (35.6 mg, 0.154 mmol) and diphenylphosphino ferrocene palladium dichloride (5.1 mg, 0.006 mmol) were dissolved in 1,4-dioxane (0.308 mL). To the resultant solution was added 2-(4-ethyl-benzyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborane (18.2 mg, 0.073 mmol), and then the solution was stirred for 3 hours at 100° C. under a nitrogen stream. The reaction solution was filtered, and the resultant product was then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (14:100)), to thereby obtain the titled compound (39.4 mg, 79%).

Workup

filtrationThe reaction solution was filtered
concentrationthe resultant product was then concentrated under reduced pressure
customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (14:100))

Sources & evidence

ORD record: ord-553da268813c4b5b9145630a3c5c33bb
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207134B2

Reaction notes

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