(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Base Information

Chemical Name:(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate
CAS No.:312730-85-1
Molecular Formula:C₄₇H₇₇NO₇SSi₂
Molecular Weight:856.368
Hs Code.:

(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Synonyms:(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Suppliers and Price of (3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

There total 21 articles about (3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate 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: 37.0%

: 189453-18-7
(1E,3S,5Z)-6-iodo-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)-1,5-heptadien-3-yl acetate

: 262375-53-1
(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

: 312730-85-1
(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Guidance literature:: (3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 28 ℃; for 1.5h; microwave irradiation;

(1E,3S,5Z)-6-iodo-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)-1,5-heptadien-3-yl acetate; With potassium phosphate; water; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃; for 1h;
DOI:10.1021/ja002024b

Reference yield:

: 184246-38-6
(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

: 312730-85-1
(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: tributylphosphine oxide / diethylaluminum chloride; R(a)-[2,2'-dihydroxy-3,3'-bis(CH₂Ph₂PO)]-1,1'-binaphthyl / CH₂Cl₂; hexane / 0.5 h / -40 °C

1.2: CH₂Cl₂; hexane / 39 h

1.3: 97 percent / trifluoroacetic acid / CH₂Cl₂; hexane / 1 h / 20 °C

2.1: 83 percent / aq. HCl / 5 h / 90 °C

3.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: 94 percent / DIBAL / toluene / 1 h / -78 °C

5.1: 68 percent / tetrahydrofuran / -78 - 20 °C

6.1: Hg(OAc)2; water / tetrahydrofuran / 2.5 h

6.2: 60 percent / tetrabutylammonium iodide / tetrahydrofuran; H₂O / 2 h

7.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C

8.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

9.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation

9.2: 37 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C

With 1H-imidazole; hydrogenchloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; Tributylphosphine oxide; mercury(II) diacetate; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; (R)-3,3'-bis(diphenylphosphinoylmethyl)-1,1'-binaphthol; diethylaluminium chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Wittig reaction;
DOI:10.1021/ja002024b

Reference yield:

: 2-Methyl-2-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-propionaldehyde

: 312730-85-1
(3S,6R,7S,8S,12Z,15S,16E)-phenyl 3,7-di-tert-butyldimethylsilyloxy-15-methoxycarbonyl-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-12,16-heptadecadienoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

1.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

2.1: K₂CO₃; SnCl₄; bis(trimethylsilyl)peroxide / trans-1,2-bisNHTs-cyclohexane; MS 4A / CH₂Cl₂ / 10 h / 0 °C

3.1: BCl₃ / CH₂Cl₂; xylene / 0.33 h / -78 °C

4.1: diisopropylethylamine / CH₂Cl₂ / 0.5 h

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation

6.2: 37 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C

With 9-borabicyclo[3.3.1]nonane dimer; bis-trimethylsilanyl peroxide; water; boron trichloride; tin(IV) chloride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; toluene; xylene; 2.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja002024b