Technology Process of (2Z,6Z,13E)-1-benzyloxy-3,8,8,14,18-pentamethyl-11-methylene-2,6,13,17-nonadecatetraen-7-yl diethyl phosphate
There total 22 articles about (2Z,6Z,13E)-1-benzyloxy-3,8,8,14,18-pentamethyl-11-methylene-2,6,13,17-nonadecatetraen-7-yl diethyl phosphate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 90 percent / PBr3 / hexane / 0.33 h / 0 °C
3: 94 percent / LiAlH4 / tetrahydrofuran / 1) 4.5h reflux 2) 2h at r.t.
4: 97 percent / pyridine / 16 h / Ambient temperature
5: 56 percent / Li / liquid ammonia; diethyl ether / 0.42 h / -33 °C
6: 90 percent / CrO3/pyridine complex / CH2Cl2 / 1.5 h / Ambient temperature
7: 1) Mg / Br(CH2)2Br / 1) ether/1h/reflux 2) 1h reflux,then 18.5h at r.t.
8: 49 percent / CrO3 (Collins reagent)-pyridine / CH2Cl2 / 8 h / Ambient temperature
9: 1) LDA / HMPA / THF, 1) 45 min at 0 deg C 2) 4h at r.t.
With
pyridine; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; phosphorus tribromide; lithium; dipyridine chromium trioxide; magnesium; ethylene dibromide; lithium diisopropyl amide;
In
tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; ammonia;
DOI:10.1021/jo01301a028
- Guidance literature:
-
Multi-step reaction with 8 steps
1: NaH / DME 1) 80-85 deg C/ 1.5 h 2a) 1h reflux 2b) 16 h at r.t.
2: 1) O3 / pyridine 2) Me2S / 1) CH2Cl2 / -78 deg C 2) r.t./overnight
3: 87 percent / NaBH4 / ethanol / 3.5 h / Ambient temperature
4: 93 percent / pyridine / 24 h / 0 °C
5: 92 percent / LiBr / acetone / 21.5 h / Heating
6: 1) Mg / Br(CH2)2Br / 1) ether/1h/reflux 2) 1h reflux,then 18.5h at r.t.
7: 49 percent / CrO3 (Collins reagent)-pyridine / CH2Cl2 / 8 h / Ambient temperature
8: 1) LDA / HMPA / THF, 1) 45 min at 0 deg C 2) 4h at r.t.
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; dimethylsulfide; dipyridine chromium trioxide; sodium hydride; ozone; magnesium; ethylene dibromide; lithium bromide; lithium diisopropyl amide;
In
pyridine; ethanol; dichloromethane; acetone;
DOI:10.1021/jo01301a028
- Guidance literature:
-
Multi-step reaction with 14 steps
1: 100 percent / LiAlH4 / tetrahydrofuran / 1) 3 h / r.t. 2) 45 min / reflux
2: 1) NaH / 1) DME / 2 h at 65-70 deg C 2) 1 h / reflux
3: 94 percent / m-Cl-C6H4-CO3H / CHCl3 / 4.5 h / Ambient temperature
4: 92.4 percent / periodic acid / dioxane; H2O / 3 h / Ambient temperature
5: 45 percent / 8N chromic acid / acetone / 0 °C
6: 1) LDA / HMPA / THF, 1) 5 min / -30 to -40 deg C 2) 2,5h r.t.
8: 94 percent / LiAlH4 / tetrahydrofuran / 1) 4.5h reflux 2) 2h at r.t.
9: 97 percent / pyridine / 16 h / Ambient temperature
10: 56 percent / Li / liquid ammonia; diethyl ether / 0.42 h / -33 °C
11: 90 percent / CrO3/pyridine complex / CH2Cl2 / 1.5 h / Ambient temperature
12: 1) Mg / Br(CH2)2Br / 1) ether/1h/reflux 2) 1h reflux,then 18.5h at r.t.
13: 49 percent / CrO3 (Collins reagent)-pyridine / CH2Cl2 / 8 h / Ambient temperature
14: 1) LDA / HMPA / THF, 1) 45 min at 0 deg C 2) 4h at r.t.
With
pyridine; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; chromic acid; lithium; dipyridine chromium trioxide; sodium hydride; magnesium; periodic acid; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; chloroform; ammonia; water; acetone;
DOI:10.1021/jo01301a028
