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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
ノート
印刷プレビュー

反応式

HRID 1092437 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]([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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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
収率 22%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8dae05976a2f4d4084f0a134fcc947b0
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129434B2

反応ノート

読み込み中…

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