(E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one

Base Information

• Chemical Name: (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one
• CAS No.: 127605-07-6
• Molecular Formula: C₃₉H₇₁O₆PSi₂
• Molecular Weight: 723.134

Synonyms:(E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one

Chemical Property of (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one

Chemical Property:

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Technology Process of (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one

There total 14 articles about (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ⁵-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-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:

(R)-cyclohex-3-enecarboxylic acid (5709-98-8) → (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ5-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one (127605-07-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) m-chloroperoxybenzoic acid, 2.) triethylamine / 1.) 0 degC, 4h, CCl₄; 2.) 55 degC, 3h

2: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 21 h / Heating

3: 98 percent / sodium bicarbonate / 3 h / 23 °C

4: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

5: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

6: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

7: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

8: 94 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / 23 °C

9: 95 percent / diisobutylaluminium hydride / hexane / 0.5 h / -78 °C

10: S,S-bromoborane corresp. to 15 / 1.) CH₂Cl₂, 23 degC, 1.5 h; 2.) CH₂Cl₂, -78 degC, 1 h

11: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

12: 95 percent / N-bromsuccinimide / acetonitrile / 1.5 h / 0 °C

13: 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) acetonitrile, 10 min, 0 degC; 2.) acetonitrile, 1 h, 22 degC

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; dmap; N-Bromosuccinimide; 2,6-di-tert-butyl-4-methylpyridine; S,S-bromoborane corresp. to 15; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In hexane; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)93750-5

Reference yield:

(1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one (116498-92-1) → (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ5-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one (127605-07-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 21 h / Heating

2: 98 percent / sodium bicarbonate / 3 h / 23 °C

3: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

4: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

5: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

6: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

7: 94 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / 23 °C

8: 95 percent / diisobutylaluminium hydride / hexane / 0.5 h / -78 °C

9: S,S-bromoborane corresp. to 15 / 1.) CH₂Cl₂, 23 degC, 1.5 h; 2.) CH₂Cl₂, -78 degC, 1 h

10: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

11: 95 percent / N-bromsuccinimide / acetonitrile / 1.5 h / 0 °C

12: 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) acetonitrile, 10 min, 0 degC; 2.) acetonitrile, 1 h, 22 degC

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; dmap; N-Bromosuccinimide; 2,6-di-tert-butyl-4-methylpyridine; S,S-bromoborane corresp. to 15; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In hexane; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)93750-5

Reference yield:

(1R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.2.1]octan-7-one (127604-95-9) → (E)-(4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-(dimethyl-phenyl-λ5-phosphanylidene)-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one (127605-07-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / sodium bicarbonate / 3 h / 23 °C

2: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / 64 h / 23 °C

3: diisobutylaluminiumhydride / hexane / 0.5 h / -78 °C

4: 1.) Li; 2.) trifluoracetic acid / 1.) THF, -20 degC, 1.5 h; 2.) THF, 0 degC, 1 h

5: R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide, boron tribromide, diisopropylethylamine / 1.) CH₂Cl₂, -45 degC, 2.5 h; 2.) CH₂Cl₂, -78 degC, 2h

6: 94 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / 23 °C

7: 95 percent / diisobutylaluminium hydride / hexane / 0.5 h / -78 °C

8: S,S-bromoborane corresp. to 15 / 1.) CH₂Cl₂, 23 degC, 1.5 h; 2.) CH₂Cl₂, -78 degC, 1 h

9: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

10: 95 percent / N-bromsuccinimide / acetonitrile / 1.5 h / 0 °C

11: 2.) 1,4-diazabicyclo<2.2.2>octane / 1.) acetonitrile, 10 min, 0 degC; 2.) acetonitrile, 1 h, 22 degC

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; R,R-1,2-diphenyl-1,2-diaminoethane bis p-nitrobenzenesulfonamide; N-Bromosuccinimide; 2,6-di-tert-butyl-4-methylpyridine; S,S-bromoborane corresp. to 15; boron tribromide; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In hexane; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)93750-5

upstream raw materials:

(E)-(4S,5S,6S)-1-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-8-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-6-methoxymethoxy-5,7-dimethyl-oct-7-en-2-one

Dimethyl(phenyl)phosphine

(R)-cyclohex-3-enecarboxylic acid

(1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one

Downstream raw materials:

(1E,8E,10E)-(3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-3-methoxymethoxy-2,4,10,12-tetramethyl-trideca-1,8,10-trien-7-one

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