(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

Base Information

Chemical Name:(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione
CAS No.:849419-01-8
Molecular Formula:C₄₅H₅₉NO₆SSi
Molecular Weight:770.118
Hs Code.:

(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

Synonyms:(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

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Chemical Property of (4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

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Technology Process of (4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

There total 14 articles about (4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione 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: 46.0%

: 849419-00-7
4-formyl-1(R)-{1-methyl-2-[2-methyl(1,3-thiazol-4-yl)]-1(E)-ethenyl}-3-(E)-butenyl-(3R,4S,5S,6R,8R)-10-dimethoxyphosphono-6-{2-(tert-butyldiphenylsilyloxy)ethyl}-3,5-isopropylidenedioxy-3,8-dimethyl-9-oxodecanoate

: (2E,4E,6E)-6-Methyl-7-(2-methyl-thiazol-4-yl)-hepta-2,4,6-trienal

: 849419-01-8
(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In toluene; at 20 ℃; for 22.5h;
DOI:10.3987/COM-04-S(P)30

Reference yield:

: 119729-76-9
ethyl (2E)(5S)-5-tert-butyldiphenylsilyloxy-6-hydroxyhex-2-enoate

: 849419-01-8
(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

2.1: 44 percent / tetrahydrofuran; hexane; diethyl ether / 12 h / -78 - 20 °C

3.1: 88 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4.1: 28 percent / n-BuLi / hexane; tetrahydrofuran / 11 h / -78 - 20 °C / Horner-Wadsworth-Emmons olefination

5.1: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h

7.1: 60 percent / AcOH; tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C

8.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 20 °C

8.2: 76 percent / DMAP / toluene / 23 h / 20 °C

9.1: 46 percent / K₂CO₃; 18-crown-6 / toluene / 22.5 h / 20 °C

With n-butyllithium; oxalyl dichloride; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Swern oxidation / 3.1: Swern oxidation / 6.1: Dess-Martin periodinane oxidation / 9.1: Horner-Emmons reaction;
DOI:10.3987/COM-04-S(P)30

Reference yield:

: 113918-79-9
dimethyl (3R,5R,6S,7S,8R)-5-<2-(3,4-dimethoxybenzyloxy)ethyl>-3,7-dimethyl-6,8-isopropylidenedioxy-2-oxo-10-undecenylphosphonate

: 849419-01-8
(4R,5S,6S,7R,9R,16S)-7-{2-(tert-butyldiphenylsilyloxy)ethyl}-4,6-isopropylidenedioxy-5,9-dimethyl-{1-methyl-2-{2-methyl-(1,3-thiazol-4-yl)}-1(E)-ethenyl}-11(E),13(E)-diene-2,10-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / DDQ / CH₂Cl₂; H₂O / 1 h

2.1: 90 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

3.1: NMO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 21 h / 20 °C

3.2: 83 percent / NaIO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 0.5 h / 20 °C

4.1: 100 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.17 h / 20 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 20 °C

5.2: 76 percent / DMAP / toluene / 23 h / 20 °C

6.1: 46 percent / K₂CO₃; 18-crown-6 / toluene / 22.5 h / 20 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; 2-methyl-but-2-ene; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 6.1: Horner-Emmons reaction;
DOI:10.3987/COM-04-S(P)30