(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

Base Information

Chemical Name:(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one
CAS No.:174657-21-7
Molecular Formula:C₅₁H₇₀O₇Si
Molecular Weight:823.198
Hs Code.:

(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

Synonyms:(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

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Chemical Property of (3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

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Technology Process of (3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

There total 34 articles about (3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-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: 42.0%

: 174657-20-6
(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S)-7-(Diethyl-isopropyl-silanyloxy)-15-hydroxy-2,14-dimethoxy-17-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,8,10,16-pentamethyl-heptadeca-2,4,10,12-tetraenoic acid

: 174657-21-7
(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; toluene; at 110 ℃; for 16h;
DOI:10.1016/0040-4039(95)02351-8

Reference yield:

: 174419-96-6
2,2-Dimethyl-propionic acid (E)-(2R,3S,4S)-3-(diethyl-isopropyl-silanyloxy)-7-iodo-2,4,6-trimethyl-hept-6-enyl ester

: 174657-21-7
(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 60 percent / <1,1'-bis(diphenylphosphino)ferrocene>palladium(II) chloride / dimethylformamide / 15 h / 50 °C

2: 79 percent / MeLi / diethyl ether / 0.5 h / 25 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) to 0 deg C, 40 min.

4: toluene / 4 h / 100 °C

5: 97 percent / DIBAL / toluene / 0.08 h / -78 °C

6: 100 percent / MnO₂ / CH₂Cl₂ / 2 h / 25 °C

7: 64 percent / 1M KOH / H₂O / 2 h / 80 °C

8: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-(dimethylamino)pyridine / 1.) THF, 25 deg C, 2 h, 2.) toluene, 110 deg C, 15 h.

With dmap; manganese(IV) oxide; potassium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; methyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo970314d

Reference yield:

: 126889-55-2
diethyl(isopropyl)silyl trifluoromethanesulfonate

: 174657-21-7
(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-8-(Diethyl-isopropyl-silanyloxy)-3,15-dimethoxy-16-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 25 °C

2: 60 percent / <1,1'-bis(diphenylphosphino)ferrocene>palladium(II) chloride / dimethylformamide / 15 h / 50 °C

3: 79 percent / MeLi / diethyl ether / 0.5 h / 25 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) to 0 deg C, 40 min.

5: toluene / 4 h / 100 °C

6: 97 percent / DIBAL / toluene / 0.08 h / -78 °C

7: 100 percent / MnO₂ / CH₂Cl₂ / 2 h / 25 °C

8: 64 percent / 1M KOH / H₂O / 2 h / 80 °C

9: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-(dimethylamino)pyridine / 1.) THF, 25 deg C, 2 h, 2.) toluene, 110 deg C, 15 h.

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; potassium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; methyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo970314d