TBS-COREY LACTONE ALDEHYDE → HCID 68733852, 화합물

HRID 1470680노트

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HRID 1470680 반응식
[Br-].[CH2:2]([PH3+])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC(C)([O-])C.[K+].[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=O)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1COCC1>[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:17])[CH3:18]

참가 물질

5

반응물 3

HCID 10989745TBS-COREY LACTONE ALDEHYDEHCID 23665647Potassium tert-butoxideHCID 86630288HCID 86630288, 화합물

생성물 1

HCID 68733852HCID 68733852, 화합물수율 91.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

n-heptylphosphonium bromide (3.185 g, 7.22 mmol) was dried under vacuum for 3 days and was then taken into dry THF (22 mL). Potassium tert-butoxide (7.2 mL, 7.2 mmol, 1 M/THF) was added and the resulting red-orange solution was stirred for 45 min. at room temperature. A solution of (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (5-1, 502 mg, 1.78 mmol, Cayman) in 7 mL THF was added by cannula, rinsing with 3 mL THF. After 1.5 h, the reaction was quenched by addition of saturated NH4Cl solution. The resulting mixture was extracted with ethyl acetate (3×) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (595 mg, 91%).

후처리

  1. washrinsing with 3 mL THF
  2. waitAfter 1.5 h
  3. customthe reaction was quenched by addition of saturated NH4Cl solution
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×)
  5. dry with materialthe combined ethyl acetate solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

출처 및 근거

ORD 기록
ord-2c611dcaa9524007ad009d5888c9284f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006464B2

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