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Triphenylphosphine → ((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene

HRID 1092437
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HRID 1092437 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]([OH:31])[CH:11]=[C:10]1[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:60][C:61]1[CH:66]=[CH:65][C:64](O)=[C:63]([CH2:68][C:69]2[CH:74]=[CH:73][C:72]([CH2:75][CH3:76])=[CH:71][CH:70]=2)[CH:62]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:34]([O:33][CH2:32][C:10]1[C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[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]([O:31][C:64]2[CH:65]=[CH:66][C:61]([Cl:60])=[CH:62][C:63]=2[CH2:68][C:69]2[CH:70]=[CH:71][C:72]([CH2:75][CH3:76])=[CH:73][CH:74]=2)[CH:11]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11432631(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enolHCID 230727454-Chloro-2-(4-ethylbenzyl)phenol

생성물 1

HCID 57741117((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene
수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a argon stream, (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enol (0.5 g, 0.933 mmol) and triphenylphosphine (367 mg, 1.400 mmol) were added to a THF (6 mL) solution of 4-chloro-2-(4-ethylbenzyl)phenol (345 mg, 1.400 mmol) at room temperature. DIAD (0.276 mL, 1.400 mmol) was added thereto at the same temperature. The reaction mixture was stirred for 48 h. The reaction mixture was concentrated under reduce pressure, and the obtained residue was purified by prepared LC-MS to obtain 157 mg of ((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene (27).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was purified
  3. customby prepared LC-MS

출처 및 근거

ORD 기록
ord-8dae05976a2f4d4084f0a134fcc947b0
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129434B2

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