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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 221921 반응식
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]
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참가 물질

6

반응물 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]

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

(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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-555057c130674e5e838d1044d97b9099
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207134B2

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