Technology Process of (3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-methylnona-3,8-dienyl)tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one
There total 13 articles about (3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-methylnona-3,8-dienyl)tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
(5-hexen-1-yl)triphenylphosphonium iodide;
With
n-butyllithium;
In
tetrahydrofuran; hexane;
at 0 ℃;
for 1h;
(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one;
In
tetrahydrofuran; hexane;
at 0 - 20 ℃;
for 2h;
DOI:10.1021/ol1026816
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 16 h / 45 °C / 760.05 Torr
2.1: diisobutylaluminium hydride / hexane / 4 h / -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
3.2: 15 h / 0 - 20 °C
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve
5.1: hydrazine / ethylene glycol / 0.5 h / 130 °C
5.2: 3 h / 230 °C
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 16 h / 45 °C
7.1: benzene / 16 h / 45 °C
8.1: water; toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C
9.2: 2 h / 0 - 20 °C
With
osmium(VIII) oxide; n-butyllithium; tetrapropylammonium perruthennate; water; palladium diacetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; hydrazine;
In
tetrahydrofuran; hexane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; benzene;
5.2: Wolff-Kishner reduction / 9.2: Wittig reaction;
DOI:10.1021/ol1026816
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: diisobutylaluminium hydride / hexane / 4 h / -78 - 20 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
2.2: 15 h / 0 - 20 °C
3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve
4.1: hydrazine / ethylene glycol / 0.5 h / 130 °C
4.2: 3 h / 230 °C
5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 16 h / 45 °C
6.1: benzene / 16 h / 45 °C
7.1: water; toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 20 °C
8.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C
8.2: 2 h / 0 - 20 °C
With
osmium(VIII) oxide; n-butyllithium; tetrapropylammonium perruthennate; water; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; hydrazine;
In
tetrahydrofuran; hexane; dichloromethane; water; ethylene glycol; mineral oil; tert-butyl alcohol; benzene;
4.2: Wolff-Kishner reduction / 8.2: Wittig reaction;
DOI:10.1021/ol1026816
