(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

Base Information

Chemical Name:(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one
CAS No.:1260612-86-9
Molecular Formula:C₂₁H₂₈O₆
Molecular Weight:376.45
Hs Code.:

Synonyms:(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

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Chemical Property of (3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

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Technology Process of (3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

There total 12 articles about (3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-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:

Reference yield: 97.0%

: 1260612-84-7
(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

: 1260612-86-9
(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

Guidance literature:: With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-72-3
(1R,5R)-ethyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-2-(trifluoromethylsulfonyloxy)cyclopent-2-enecarboxylate

: 1260612-86-9
(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

Guidance literature:: Multi-step reaction with 8 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

With osmium(VIII) oxide; 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;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-73-4
(1R,5R)-1-ethyl 2-methyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-ene-1,2-dicarboxylate

: 1260612-86-9
(3aR,4S,5R,6aR)-3a-((4-methoxybenzyloxy)methyl)-4,5-dimethyl-4-(3-oxobutyl)-tetrahydro-3aH-cyclopenta(d)(1,3)dioxol-2-one

Guidance literature:: Multi-step reaction with 7 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

With osmium(VIII) oxide; 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;
DOI:10.1021/ol1026816