Technology Process of 1-((4S,5S)-2,2-Dimethyl-5-pent-3-ynyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienecarboxylic acid
There total 7 articles about 1-((4S,5S)-2,2-Dimethyl-5-pent-3-ynyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienecarboxylic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
benzoic acid;
With
lithium;
In
ammonia;
at -49 ℃;
for 0.166667h;
(4R,5S)-4-(Bromomethyl)-2,2-dimethyl-5-(pent-3-ynyl)-1,3-dioxolane;
In
diethyl ether; ammonia;
for 0.75h;
DOI:10.1135/cccc20000490
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 90 percent / pyridine / 3 h / 20 °C
2.1: CH3Li / dioxane; diethyl ether / 0.5 h / 0 °C
2.2: dioxane / 15 h / Heating
3.1: 58 percent / TsOH / methanol / 12 h / Heating
4.1: 87 percent / Red-Al / toluene; diethyl ether / 2 h / 20 °C
5.1: 95 percent / 1,2-bis(diphenylphosphino)ethane; bromine / CH2Cl2 / 3 h / 20 °C
6.1: AD-mix α; NaHCO3; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 26 h / 0 °C
6.2: 74 percent / pyridinium tosylate / acetone / 35 h / 20 °C
7.1: Li / liquid ammonia / 0.17 h / -49 °C
7.2: diethyl ether; liquid ammonia / 0.75 h
With
pyridine; AD-mix-α; methanesulfonamide; methyllithium; bromine; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 1,2-bis-(diphenylphosphino)ethane;
In
1,4-dioxane; methanol; diethyl ether; dichloromethane; ammonia; water; toluene; tert-butyl alcohol;
1.1: Tosylation / 2.1: Metallation / 2.2: Condensation / 3.1: Substitution / 4.1: Reduction / 5.1: Substitution / 6.1: Epoxidation / 6.2: Cyclization / 7.1: Reduction / 7.2: Alkylation;
DOI:10.1135/cccc20000490
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 87 percent / Red-Al / toluene; diethyl ether / 2 h / 20 °C
2.1: 95 percent / 1,2-bis(diphenylphosphino)ethane; bromine / CH2Cl2 / 3 h / 20 °C
3.1: AD-mix α; NaHCO3; MeSO2NH2 / H2O; 2-methyl-propan-2-ol / 26 h / 0 °C
3.2: 74 percent / pyridinium tosylate / acetone / 35 h / 20 °C
4.1: Li / liquid ammonia / 0.17 h / -49 °C
4.2: diethyl ether; liquid ammonia / 0.75 h
With
AD-mix-α; methanesulfonamide; bromine; lithium; sodium hydrogencarbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; 1,2-bis-(diphenylphosphino)ethane;
In
diethyl ether; dichloromethane; ammonia; water; toluene; tert-butyl alcohol;
1.1: Reduction / 2.1: Substitution / 3.1: Epoxidation / 3.2: Cyclization / 4.1: Reduction / 4.2: Alkylation;
DOI:10.1135/cccc20000490
