(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

Base Information

• Chemical Name: (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
• CAS No.: 159179-13-2
• Molecular Formula: C₅₁H₈₄O₅Si₂
• Molecular Weight: 833.396

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (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

There total 28 articles about (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 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: 50.0%

(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) → (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 (159179-13-2)

Guidance literature:

With (S)-B-methyl oxazaborolidine; benzo[1,3,2]dioxaborole; at -30 ℃; for 36h;

DOI:10.1021/ja00095a078

Reference yield:

(3S,4R)-4-Methoxy-3-(4-methoxy-benzyloxy)-pentanal → (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 (159179-13-2)

Guidance literature:

Multi-step reaction with 15 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

15: 50 percent / (S)-B-methyl oxazaborolidine, catecholborane / 36 h / -30 °C

With 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; (S)-B-methyl oxazaborolidine; 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; benzo[1,3,2]dioxaborole; 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)-(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 (159179-13-2)

Guidance literature:

Multi-step reaction with 17 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

17: 50 percent / (S)-B-methyl oxazaborolidine, catecholborane / 36 h / -30 °C

With 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; n-butyllithium; mercury(II) perchlorate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tributylphosphine; (S)-B-methyl oxazaborolidine; 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; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00095a078

upstream raw materials:

(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

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

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

3-[(2S,5S)-5-((R)-1-Methoxy-ethyl)-tetrahydro-furan-2-yl]-propionaldehyde

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