Tetrabutylammonium Fluoride Trihydrate → benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

HRID 703687

반응식

HRID 703687 반응식
[CH2:1]([C@@H:7]([C@@H:18]([O:39][Si](C(C)(C)C)(C)C)[CH2:19][C@H:20]([O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([C@@H:7]([C@@H:18]([OH:39])[CH2:19][C@H:20]([O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

4

반응물 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67935903benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

생성물 1

HCID 67935914benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate수율 60.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

480 mg of benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyl-dimethylsilyl)oxy]-5 -[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate and 350 mg of tetrabutylammonium fluoride trihydrate are dissolved in 8 ml of THF and stirred for 12 hours. After evaporation the residue is dissolved in 50 ml of ether and washed with water. The ethereal phase is dried and evaporated. The crude product is chromatographed on silica gel. There are obtained 240 mg of benzyl (2S,3S,5R)-2-hexyl-3-hydroxy-5 -[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate,, MS: 463 [(M+H)+ -dihydro-2H-pyran-2-yl].

후처리

  1. customAfter evaporation the residue
  2. dissolutionis dissolved in 50 ml of ether
  3. washwashed with water
  4. customThe ethereal phase is dried
  5. customevaporated
  6. customThe crude product is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-7ebec7ebb6004bc180167b4dc1b4b8e3
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983746

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