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

反応式

HRID 221938 の反応式
[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

参加物

5

反応物 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]

生成物 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]収率 98.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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%).

後処理

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

出典と根拠

ORDレコード
ord-4e9a8741fe224381bf4542b154d9c8ba
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

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