trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

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Chemical Name:trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone
CAS No.:114489-14-4
Molecular Formula:C₃₆H₆₈O₄Si₂
Molecular Weight:621.105
Hs Code.:

Synonyms:trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

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Chemical Property of trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

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Technology Process of trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

There total 24 articles about trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone 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:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 114489-14-4
trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / PPh₃, CBr₄ / acetonitrile / Ambient temperature

2: 70 percent / azobisisobutyronitryle / toluene / 30 h / Heating

3: 1. O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) -78 deg C, 1 h

4: various solvent(s) / 40 h / Heating

With dimethylsulfide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; ozone; triphenylphosphine; In toluene; acetonitrile;
DOI:10.1021/jo00247a014

Reference yield:

: 4286-55-9
1-bromo-6-hexanol

: 114423-67-5,114489-14-4,114489-15-5
trans,trans-5-<9'-(2'',3''-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / Et₃N, bis(trimethylsilyl)amine / tetrahydrofuran / Ambient temperature

3: 1.) BH₃*Me₂S, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, RT, 3 days 2.) 1 h

4: 84 percent / CBr₄, PPh₃ / acetonitrile / 1 h / 0 °C

5: 95 percent / lutidine / CH₂Cl₂ / 0 - 20 °C

6: acetonitrile / 72 h / Heating

7: 1.) NaN(TMS)2 / 1a.) THF, 0 deg C, 1b.) reflux, 90 min, 2a.) -78 deg C, 30 min, 2b.) RT, 14 h

8: 99 percent / K₂CO₃ / methanol / 1.5 h / Ambient temperature

9: (COCl)2, DMSO / CH₂Cl₂ / 0.25 h / -50 °C

10: LAH, CrCl₃ / tetrahydrofuran / Ambient temperature

With chromium chloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; carbon tetrabromide; dimethylsulfide borane complex; lutidine; dihydrogen peroxide; sodium hexamethyldisilazane; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00247a014

Reference yield:

: 4286-55-9
1-bromo-6-hexanol

: 114489-14-4
trans,trans-(5S)-5-<9'-(2,3-bis((dimethylthexylsilyl)oxy)cyclohexyl)-3'-nonenyl>-3-methylenetetrahydro-2-furanone

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / Et₃N, bis(trimethylsilyl)amine / tetrahydrofuran / Ambient temperature

3: 1.) BH₃*Me₂S, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, RT, 3 days 2.) 1 h

4: 84 percent / CBr₄, PPh₃ / acetonitrile / 1 h / 0 °C

5: 95 percent / lutidine / CH₂Cl₂ / 0 - 20 °C

6: acetonitrile / 72 h / Heating

7: various solvent(s) / 40 h / Heating

With sodium hydroxide; carbon tetrabromide; dimethylsulfide borane complex; lutidine; dihydrogen peroxide; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo00247a014