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ChemicalBook CAS DataBase List Lipstatin

Lipstatin synthesis

6synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 11 steps
1: 100 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
2: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating
3: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C
4: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT
5: 100 percent / acetonitrile / 48 h / Heating
6: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
7: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
8: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
9: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
10: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
11: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT

References:

Pons, Jean-Marc;Pommier, Agnes;Lerpiniere, Joan;Kocienski, Philip [Journal of the Chemical Society. Perkin transactions I,1993,# 14,p. 1549 - 1552]

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