Methanol → (3'r,4's,5s,5's,6'r)-3-[(4-Ethylphenyl)methyl]-6'-hydroxymethyl-3',4',5',6'-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]-3',4',5'-triol

HRID 221921

Reaktionsgleichung

Reaktionsgleichung von HRID 221921
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:47]1[CH:46]=[C:45]3[C:48]([CH2:51][C:52]4[CH:57]=[CH:56][C:55]([CH2:58][CH3:59])=[CH:54][CH:53]=4)=[CH:49][S:50][C:44]3=[CH:43][C:42]=1[CH2:41][O:40]2)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.B(Cl)(Cl)Cl.CO>ClCCl>[CH2:58]([C:55]1[CH:54]=[CH:53][C:52]([CH2:51][C:48]2[C:45]3[C:44](=[CH:43][C:42]4[CH2:41][O:40][C@:10]5([C:47]=4[CH:46]=3)[C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]5)[S:50][CH:49]=2)=[CH:57][CH:56]=1)[CH3:59]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 12784PentamethylbenzeneHCID 25135Boron TrichlorideHCID 91310466(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]

Produkt 1

HCID 24831316(3'r,4's,5s,5's,6'r)-3-[(4-Ethylphenyl)methyl]-6'-hydroxymethyl-3',4',5',6'-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]-3',4',5'-triol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(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] (34.1 mg, 0.042 mmol) was dissolved in dichloromethane (1.4 mL). To the resultant solution was added pentamethylbenzene (94.3 mg, 0.636 mmol), and then the solution was cooled to −78° C. Boron trichloride (1.0 M dichloromethane solution, 0.212 mL) was added dropwise, and the solution was stirred for 3 hours. To the solution was then added methanol (1.5 mL) to stop the reaction. The temperature of the solution was raised to room temperature. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (2:25)), and the resultant product was then further isolated and purified by reverse phase HPLC (developing solution=acetonitrile:water (35:65 to 100:0)), to thereby obtain the titled compound (13.3 mg, 70%).

Aufarbeitung

  1. customthe reaction
  2. temperatureThe temperature of the solution was raised to room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (2:25))

Quellen und Nachweise

ORD-Eintrag
ord-555057c130674e5e838d1044d97b9099
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207134B2

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