methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

Base Information

Chemical Name:methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester
CAS No.:91111-18-1
Molecular Formula:C₂₁H₂₅F₃O₆
Molecular Weight:430.421
Hs Code.:

Synonyms:methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

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Chemical Property of methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

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Technology Process of methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

There total 8 articles about methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester 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: 88.0%

: 39637-99-5,20445-33-4
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

: 91199-05-2
(+)-(6S,8R,E)-methyl 2,3-didehydrononactate

: 91111-18-1
methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

Guidance literature:: With dmap; In tetrahydrofuran; at 0 ℃; for 4h;
DOI:10.1021/ja00330a045

Reference yield:

: 91111-13-6
(S)-octa-1,7-dien-4-ol

: 91111-18-1
methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / n-butyllithium / hexane; diethyl ether; tetrahydrofuran / 4 h

2: iodine / acetonitrile / 10 h / -20 °C

3: 98 percent / tri-n-butyltin hydride / tetrahydrofuran / 36 h / 40 °C

4: ozone / methanol / -78 °C

5: 85 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

6: Jones reagent / acetone / 0.17 h / 0 °C

7: 1.) K₂CO₃; 2.) oxalic acid dihydrate / 1.) methanol, 21 deg C, 9 h; 2.) dichloromethane, reflux 4 h

8: 88 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 0 °C

With dmap; n-butyllithium; jones reagent; iodine; tri-n-butyl-tin hydride; oxalic acid; titanium tetrachloride; potassium carbonate; ozone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; acetonitrile;
DOI:10.1021/ja00330a045

Reference yield:

: 91111-14-7
(4S,6R)-4-(3-butenyl)-6-methyl-1,3-dioxan-2-one

: 91111-18-1
methyl (6R,8S)-(E)-2,3-dehydrononactate (S)-(-)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoate ester

Guidance literature:: Multi-step reaction with 5 steps

1: ozone / methanol / -78 °C

2: 85 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

3: Jones reagent / acetone / 0.17 h / 0 °C

4: 1.) K₂CO₃; 2.) oxalic acid dihydrate / 1.) methanol, 21 deg C, 9 h; 2.) dichloromethane, reflux 4 h

5: 88 percent / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 0 °C

With dmap; jones reagent; oxalic acid; titanium tetrachloride; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1021/ja00330a045