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

Base Information

Chemical Name: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
CAS No.:849419-00-7
Molecular Formula:C₄₇H₆₆NO₁₀PSSi
Molecular Weight:896.167
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 12 articles about 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 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: 76.0%

: 849418-90-2
(2E,6E)(5S)-5-hydroxy-6-methyl-7-{2-methyl-(1,3-thiazol-4-yl)}hepta-2,6-dienal

: 849418-89-9
(3R,4S,5S,6R,8R)-10-dimethoxyphosphono-6-{2-(tert-butyldiphenylsilyloxy)ethyl}-3,5-isopropylidenedioxy-3,8-dimethyl-9-oxodecanoic acid

: 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

Guidance literature:: (3R,4S,5S,6R,8R)-10-dimethoxyphosphono-6-{2-(tert-butyldiphenylsilyloxy)ethyl}-3,5-isopropylidenedioxy-3,8-dimethyl-9-oxodecanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

(2E,6E)(5S)-5-hydroxy-6-methyl-7-{2-methyl-(1,3-thiazol-4-yl)}hepta-2,6-dienal; With dmap; In toluene; at 20 ℃; for 23h;
DOI:10.3987/COM-04-S(P)30

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

With n-butyllithium; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 3.1: Swern oxidation / 6.1: Dess-Martin periodinane oxidation;
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

: 849419-00-7
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

Guidance literature:: Multi-step reaction with 5 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

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