반응 #1879369

ord-d3e80b1865d34207a9241eaeb472ffcb

반응 방정식

CCC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-ethylpregna-5,7,16-triene
CC[Si](CC)(CC)OC(C)(C)C/C=C\Br
1-bromo-4-triethylsilyloxy-4-methyl-(2Z)-pentene
[H-].[Na+]
sodium hydride
C1COCCOCCOCCOCCO1
15-crown-5
→
CCC(C)(O/C=C\CC(C)(C)O[Si](CC)(CC)CC)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
titled compound
수율 100.0%
CCC(C)(O/C=C\CC(C)(C)O[Si](CC)(CC)CC)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-bis(tert-butyldimethylsilyloxy)-20-{4-triethylsilyloxy-4-methyl-(2Z)-pentenyloxy}-20-ethylpregna-5,7,16-triene
수율 100.0%

반응물

CCC(C)(O)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-ethylpregna-5,7,16-triene
CC[Si](CC)(CC)OC(C)(C)C/C=C\Br
1-bromo-4-triethylsilyloxy-4-methyl-(2Z)-pentene
[H-].[Na+]
sodium hydride
C1COCCOCCOCCOCCO1
15-crown-5

시약

없음

용매

C1CCOC1
tetrahydrofuran

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도of Example 5(1) (reflux under heating for 1 hour)
  2. 2
    기타purified by column chromatography (hexane:toluene=1:1)

실험 절차

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-ethylpregna-5,7,16-triene (103 mg, 0.180 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2Z)-pentene (211 mg, 0.719 mol), sodium hydride (60% in oil, 43 mg, 1.08 mmol), 15-crown-5 (40 mg, 0.182 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (reflux under heating for 1 hour), worked up and purified by column chromatography (hexane:toluene=1:1) to give the titled compound (141 mg, 100%) as a colorless solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07074777B2uspto-grants-2006_07