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

HRID 221938

Reaktionsgleichung

Reaktionsgleichung von HRID 221938
[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]([C:55]4[CH:60]=[CH:59][C:58]([CH2:61][CH3:62])=[CH:57][CH:56]=4)=[C:49]([Si](C)(C)C)[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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[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:26]=[CH:27][CH:28]=[CH:29][CH:30]=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]([C:55]4[CH:56]=[CH:57][C:58]([CH2:61][CH3:62])=[CH:59][CH:60]=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

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 11078149TBAF tetrahydrofuranHCID 68505591(3'r,4's,5s,5's,6'r)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-3-(4-ethylphenyl)-3',4',5',6'-tetrahydro-2-trimethylsilyl-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]

Produkt 1

HCID 68506275(3'r,4's,5s,5's,6'r)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-3-(4-ethylphenyl)-3',4',5',6'-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]Ausbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-(4-ethylphenyl)-3′,4′,5′,6′-tetrahydro-2-trimethylsilyl-spiro[thieno[2,3,f]isobenzofuran-5(7H),2′-[2H]pyran] (0.094 g, 0.109 mmol) was dissolved in tetrahydrofuran (0.5 mL). A Solution of tetrabutylammonium fluoride/tetrahydrofuran (1.0 M, 0.43 mL) was added thereto, and then the mixture was stirred for 1.5 hours at room temperature. Saturated aqueous ammonium chloride was added thereto, and the resultant mixture was extracted with diethyl ether. The organic layer was concentrated under reduced pressure, to thereby obtain the titled compound (84.5 mg, 98%).

Aufarbeitung

  1. extractionthe resultant mixture was extracted with diethyl ether
  2. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4e9a8741fe224381bf4542b154d9c8ba
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207134B2

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