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Triphenylphosphine → ({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane

HRID 1397550
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HRID 1397550 반응식
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:13][C@@H:12](O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1C=CC(OP(OC2C=CC=CC=2)([N:64]=[N+:65]=[N-:66])=O)=CC=1>C1COCC1>[N:64]([C@H:12]1[CH2:13][C@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11]1)=[N+:65]=[N-:66]
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 123414Diphenylphosphoryl azideHCID 5462977Diethyl azodicarboxylateHCID 66798092(1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanol

생성물 1

HCID 86618712({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane수율 63%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)-silyl]oxy}cyclopentanol (138.9 mg, 0.0004127 mol) and PPh3 (118 mg, 0.000451 mol) in THF (2.7 mL) at 0° C. was slowly added DEAD (71.1 μL, 0.000451 mol). The reaction was stirred for 5 minutes, then diphenylphosphonic azide (97.4 μL, 0.000452 mol) was added dropwise. The mixture was stirred for one hour. The reaction was partitioned with water and EtOAc. The layers were separated and the aqueous extracted with EtOAc (2×). The combined organics were washed with brine (1×), dried (Na2SO4), filtered, and collected in vacuo. The residue was purified by flash chromatography (0 to 10% EtOAc/hexanes) to obtain 93.5 mg (63%) of the title compound.

후처리

  1. customat 0° C.
  2. stirringThe mixture was stirred for one hour
  3. customThe reaction was partitioned with water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous extracted with EtOAc (2×)
  6. washThe combined organics were washed with brine (1×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customcollected in vacuo
  10. customThe residue was purified by flash chromatography (0 to 10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-1b588623dfe24a03b595996b5b31f881
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901136B2

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