(1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one

Base Information

• Chemical Name: (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one
• CAS No.: 159179-12-1
• Molecular Formula: C₅₁H₈₂O₅Si₂
• Molecular Weight: 831.38

Synonyms:(1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one

Chemical Property of (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one

There total 27 articles about (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-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:

(3S,4R)-4-Methoxy-3-(4-methoxy-benzyloxy)-pentanal → (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one (159179-12-1)

Guidance literature:

Multi-step reaction with 14 steps

1: tetrahydrofuran / -78 °C

2: imidazole / dimethylformamide / 60 °C

3: DDQ, H₂O / CH₂Cl₂ / 0 °C

4: 55 percent / Pd(OAc)2 / 23 °C

5: 100 percent / Bu₄NF / tetrahydrofuran / 0 °C

6: 1.) 2,2'-dibenzothiazolyl disulfide, Bu₃P, 2.) Bu₃SnH, AIBN / 1.) toluene, reflux, 2.) benzene, 80 deg C

7: 91 percent / LAH / tetrahydrofuran / 0 °C

8: 98 percent / CBr₄, PPh₃ / CH₂Cl₂ / 0 - 23 °C

9: 67 percent / tetrahydrofuran / -25 °C

10: 73 percent / Hg(ClO₄)2, CaCO₃ / tetrahydrofuran; H₂O

11: 1.) NaN(TMS)2 / 1.) THF, 23 deg C, 2.) THF, -78 deg C to 23 deg C

12: 70 percent / TBAF / tetrahydrofuran / -78 - 23 °C

13: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

14: 1.) n-BuLi, 3.) oxalyl chloride

With 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; di(benzothiazol-2-yl)disulfide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00095a078

Reference yield:

(2R,3S)-5,5-Bis-ethylsulfanyl-3-(4-methoxy-benzyloxy)-pentan-2-ol (208713-50-2) → (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one (159179-12-1)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) NaH / tetrahydrofuran / 0 °C

2: 94 percent / HgCl₂, CaCO₃ / acetonitrile; H₂O / 0 °C

3: tetrahydrofuran / -78 °C

4: imidazole / dimethylformamide / 60 °C

5: DDQ, H₂O / CH₂Cl₂ / 0 °C

6: 55 percent / Pd(OAc)2 / 23 °C

7: 100 percent / Bu₄NF / tetrahydrofuran / 0 °C

8: 1.) 2,2'-dibenzothiazolyl disulfide, Bu₃P, 2.) Bu₃SnH, AIBN / 1.) toluene, reflux, 2.) benzene, 80 deg C

9: 91 percent / LAH / tetrahydrofuran / 0 °C

10: 98 percent / CBr₄, PPh₃ / CH₂Cl₂ / 0 - 23 °C

11: 67 percent / tetrahydrofuran / -25 °C

12: 73 percent / Hg(ClO₄)2, CaCO₃ / tetrahydrofuran; H₂O

13: 1.) NaN(TMS)2 / 1.) THF, 23 deg C, 2.) THF, -78 deg C to 23 deg C

14: 70 percent / TBAF / tetrahydrofuran / -78 - 23 °C

15: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

16: 1.) n-BuLi, 3.) oxalyl chloride

With 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; di(benzothiazol-2-yl)disulfide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; mercury dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00095a078

Reference yield:

(2R,3S)-5,5-Bis-ethylsulfanyl-3-(4-methoxy-benzyloxy)-pentane-1,2-diol (208713-49-9) → (1E,7Z)-(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-one (159179-12-1)

Guidance literature:

Multi-step reaction with 19 steps

1: pyridine / -5 °C

2: NaOMe / diethyl ether / 0 °C

3: LAH / tetrahydrofuran / 0 °C

4: 1.) NaH / tetrahydrofuran / 0 °C

5: 94 percent / HgCl₂, CaCO₃ / acetonitrile; H₂O / 0 °C

6: tetrahydrofuran / -78 °C

7: imidazole / dimethylformamide / 60 °C

8: DDQ, H₂O / CH₂Cl₂ / 0 °C

9: 55 percent / Pd(OAc)2 / 23 °C

10: 100 percent / Bu₄NF / tetrahydrofuran / 0 °C

11: 1.) 2,2'-dibenzothiazolyl disulfide, Bu₃P, 2.) Bu₃SnH, AIBN / 1.) toluene, reflux, 2.) benzene, 80 deg C

12: 91 percent / LAH / tetrahydrofuran / 0 °C

13: 98 percent / CBr₄, PPh₃ / CH₂Cl₂ / 0 - 23 °C

14: 67 percent / tetrahydrofuran / -25 °C

15: 73 percent / Hg(ClO₄)2, CaCO₃ / tetrahydrofuran; H₂O

16: 1.) NaN(TMS)2 / 1.) THF, 23 deg C, 2.) THF, -78 deg C to 23 deg C

17: 70 percent / TBAF / tetrahydrofuran / -78 - 23 °C

18: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C

19: 1.) n-BuLi, 3.) oxalyl chloride

With pyridine; 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; di(benzothiazol-2-yl)disulfide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium methylate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00095a078

upstream raw materials:

tert-butyldimethylsilyl chloride

(Z)-(S)-8-[(2R,5S)-5-((R)-1-Methoxy-ethyl)-tetrahydro-furan-2-yl]-2-methyl-oct-5-enal

2-[(2S,5S)-5-((R)-1-Methoxy-ethyl)-tetrahydro-furan-2-yl]-ethanol

(3R,5S,6R)-6-Methoxy-hept-1-ene-3,5-diol

Downstream raw materials:

(1E,7Z)-(3S,4S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-1-{(1R,2S,3S)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexyl}-10-[(2R,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-1,7-dien-3-ol

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