methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

Base Information

Chemical Name:methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate
CAS No.:1429480-89-6
Molecular Formula:C₂₉H₄₄O₆
Molecular Weight:488.665
Hs Code.:

Synonyms:

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Chemical Property of methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

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Technology Process of methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

There total 10 articles about methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate 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:

: C₁₇H₂₂O₆

: 60669-22-9
n-undecyltriphenylphosphonium bromide

: 18107-18-1
diazomethyl-trimethyl-silane

: 1429480-89-6
methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

: 1429480-90-9
methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

Guidance literature:: n-undecyltriphenylphosphonium bromide; With n-butyllithium; In hexane; dimethyl sulfoxide; at 20 - 200 ℃; for 2h; Inert atmosphere;

C₁₇H₂₂O₆; In hexane; dimethyl sulfoxide; at 20 - 120 ℃; for 4h; Inert atmosphere;

diazomethyl-trimethyl-silane; Overall yield = 210mg; Further stages;
DOI:10.1021/jo400263w

Reference yield:

: 100-39-0
benzyl bromide

: 1429480-89-6
methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3.1: dirhodium tetraacetate / benzene / 1 h / Inert atmosphere; Reflux

4.1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / Inert atmosphere; Reflux

5.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 7 h / 20 - 70 °C / Inert atmosphere

6.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: water; toluene-4-sulfonic acid / acetone / 12.5 h / 20 °C / Inert atmosphere; Reflux

9.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere

10.1: n-butyllithium / hexane; dimethyl sulfoxide / 2 h / 20 - 200 °C / Inert atmosphere

10.2: 4 h / 20 - 120 °C / Inert atmosphere

With indium(III) triflate; dirhodium tetraacetate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; mineral oil; benzene;
DOI:10.1021/jo400263w

Reference yield:

: 1429480-79-4
1-(((S)-2-(benzyloxy)but-3-ynyloxy)methyl)-4-methoxybenzene

: 1429480-89-6
methyl (4aS,7R,7aS)-7-(benzyloxy)-4a-(dodec-1-enyl)-tetrahydro-2,2-dimethyl-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2.1: dirhodium tetraacetate / benzene / 1 h / Inert atmosphere; Reflux

3.1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / Inert atmosphere; Reflux

4.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 7 h / 20 - 70 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: water; toluene-4-sulfonic acid / acetone / 12.5 h / 20 °C / Inert atmosphere; Reflux

8.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere

9.1: n-butyllithium / hexane; dimethyl sulfoxide / 2 h / 20 - 200 °C / Inert atmosphere

9.2: 4 h / 20 - 120 °C / Inert atmosphere

With indium(III) triflate; dirhodium tetraacetate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; water; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetone; toluene; benzene;
DOI:10.1021/jo400263w