Octyltriphenylphosphonium bromide → (2S,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-4-methoxy-5-methyl-2-[(Z)-1-nonenyl]tetrahydro-2H-pyran

HRID 2399561

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HRID 2399561 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Li]CCCC.[CH3:34][O:35][C@H:36]1[C@@H:41]([CH3:42])[CH2:40][O:39][C@H:38]([CH:43]=O)[C@@H:37]1[O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Si:46]([O:45][C@@H:37]1[C@@H:36]([O:35][CH3:34])[C@@H:41]([CH3:42])[CH2:40][O:39][C@H:38]1/[CH:43]=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:47])[CH3:48]

참가 물질

6

반응물 3

HCID 3084855Octyltriphenylphosphonium bromideHCID 57231418(2S,3R,4S,5S)-4-methoxy-5-methyl-3-(tert-butyldimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehydeHCID 178418339Butyllithium

생성물 1

HCID 67805109(2S,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-4-methoxy-5-methyl-2-[(Z)-1-nonenyl]tetrahydro-2H-pyran수율 90.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 12679Hexamethylphosphoramide용매

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온도
0 °C

실험 절차

To a stirred solution of n-octyltriphenylphosphonium bromide (2124 mg) in dry THF (10 ml) and dry HMPA (5 ml), there was added n-BuLi (4.0 ml, 1.6M in n-hexane) at 0° C. After the mixture was stirred at 0° C. for 30 min, a solution of (2S,3R,4S,5S)-4-methoxy-5-methyl-3-(tert-butyldimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde (497 mg) in dry THF (3 ml) was added to the resulting orange solution. The mixture was stirred at 0° C. for 30 min, and at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride solution. The mixture was extracted with diethyl ether, and the combined ethereal extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography gave (2S,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-4-methoxy-5-methyl-2-[(Z)-1-nonenyl]tetrahydro-2H-pyran (602 mg, 72% yield).

후처리

  1. stirringThe mixture was stirred at 0° C. for 30 min
  2. waitat room temperature for 2 hours
  3. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe combined ethereal extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by silica gel chromatography

출처 및 근거

ORD 기록
ord-a9a10f0178f34d54ae45898b879aa968
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05449785

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