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

반응식

HRID 221938 반응식
[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

참가 물질

5

반응물 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]

생성물 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]수율 98.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(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%).

후처리

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

출처 및 근거

ORD 기록
ord-4e9a8741fe224381bf4542b154d9c8ba
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207134B2

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