(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

Base Information

Chemical Name:(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one
CAS No.:442913-68-0
Molecular Formula:C₂₃H₃₂O₆
Molecular Weight:404.503
Hs Code.:

Synonyms:(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

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Chemical Property of (E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

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Technology Process of (E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

There total 12 articles about (E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-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: 82.0%

: 442913-67-9
(S)-2-(4-Methoxy-benzyloxy)-hex-5-enoic acid (S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-butyl ester

: (Z)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

: 442913-68-0
(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

Guidance literature:: ruthenium indenylidene; In dichloromethane; for 4h; Heating;
DOI:10.1021/ja020238i

Reference yield:

: 141979-56-8
1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside

: 442913-68-0
(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: TMSOTf / acetonitrile / 24 h / 0 °C

1.2: H₂ / Pd/C / CH₂Cl₂ / 3 h / 20 °C / 760.05 Torr

2.1: 380 mg / MeONa / methanol / 4 h / 20 °C

3.1: 89 percent / iodine; PPh₃; imidazole / CH₂Cl₂ / 20 h / 20 °C

4.1: 86 percent / Zn(Ag)-graphite / tetrahydrofuran / 0.5 h / 20 °C

5.1: 87 percent / DCC; DMAP / CH₂Cl₂ / 28 h / 20 °C

6.1: 82 percent / ruthenium indenylidene complex / CH₂Cl₂ / 4 h / Heating

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; iodine; sodium methylate; dicyclohexyl-carbodiimide; triphenylphosphine; ruthenium indenylidene; silver; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja020238i

Reference yield:

: 442913-66-8
(S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)butan-1-ol

: 442913-68-0
(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / DCC; DMAP / CH₂Cl₂ / 28 h / 20 °C

2: 82 percent / ruthenium indenylidene complex / CH₂Cl₂ / 4 h / Heating

With dmap; dicyclohexyl-carbodiimide; ruthenium indenylidene; In dichloromethane;
DOI:10.1021/ja020238i