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Tributylphosphine → 1-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene

HRID 554563
ノート
印刷プレビュー

反応式

HRID 554563 の反応式
[CH:1]1([C:4]2[CH:17]=[CH:16][C:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[OH:15])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.[CH2:31]([O:38][C@H:39]1[C@H:44]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:43]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@@H:42](O)[CH:41]=[C:40]1[CH2:62][O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN(C(/N=N/C(N(C)C)=O)=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH:1]1([C:4]2[CH:17]=[CH:16][C:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C@H:42]3[C@H:43]([O:53][CH2:54][C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C@@H:44]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@H:39]([O:38][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:40]([CH2:62][O:63][CH2:64][C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)=[CH:41]3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 13831TributylphosphineHCID 5353800DiamideHCID 11432631(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enolHCID 674614742-(4-Cyclopropylbenzyl)phenol

生成物 1

HCID 674611171-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene収率 62%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

In a nitrogen stream, 2-(4-cyclopropylbenzyl)phenol and tributylphosphine (70 μL, 0.28 mmol) were added to a solution of (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enol (51 mg, 0.095 mmol) as described in a document [J. Org. Chem., 63, 5668-5671 (1998)] in toluene (300 μL) under cooling with ice, and then tetramethylazodicarboxamide (48 mg, 0.28 mmol) was added thereto at the same temperature. The reaction mixture was stirred at the same temperature for 20 hours and then hexane was added thereto and the precipitate was filtered and the solvent of the filtrate was distilled. The obtained residue was purified by preparative TLC [developing solution=ethyl acetate:n-hexane (1:5) to obtain the title compound (44 mg, 62%).

後処理

  1. temperatureunder cooling with ice
  2. filtrationthe precipitate was filtered
  3. distillationthe solvent of the filtrate was distilled
  4. customThe obtained residue was purified by preparative TLC [

出典と根拠

ORDレコード
ord-a367b2c831964a86a98f07df5923cfa5
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048897B2

反応ノート

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