(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

Base Information

Chemical Name:(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol
CAS No.:474411-14-8
Molecular Formula:C₃₉H₇₁NO₁₀Si₂
Molecular Weight:770.164
Hs Code.:

(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

Synonyms:(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

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Chemical Property of (2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

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Technology Process of (2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

There total 19 articles about (2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol 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: 91.0%

: (4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dienoic acid methyl ester

: 474411-14-8
(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃; for 1h;
DOI:10.1021/ol0267432 DOI:10.1021/jo034870l

Reference yield:

: 474411-08-0
(2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-6-(5-nitro-2,3,6-trimethoxy-phenyl)-hexanal

: 474411-14-8
(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

Guidance literature:: Multi-step reaction with 18 steps

1.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 °C

2.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C

3.2: 98 percent / diethyl ether / 2 h / 20 °C

4.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

5.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 °C

5.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

6.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

8.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

9.1: 93 percent / toluene / 7 h / 90 °C

10.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C

11.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

12.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂ / 2.5 h / -78 °C

12.2: 92 percent / CH₂Cl₂ / 3 h / -78 °C

13.1: aq. LiOH / tetrahydrofuran / 0 - 20 °C

14.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C

15.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

16.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

17.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.17 h / -78 °C

17.2: 81 percent / tetrahydrofuran; toluene / 4 h / -78 °C

18.1: 91 percent / DIBAL-H / diethyl ether; toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; lithium hydroxide; borane-THF; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; hydrogen fluoride; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 3.2: Wittig reaction;
DOI:10.1021/jo034870l

Reference yield:

: 474410-96-3
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

: 474411-14-8
(2Z,4S,5S,6E,8S,9R,12R,10S)-9-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-13-(3-nitro-2,5,6-trimethoxy-phenyl)-6,8,12-trimethyl-5-(triethyl-silanyloxy)-trideca-2,6-dien-1-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 °C

2.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

5.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

6.1: 93 percent / toluene / 7 h / 90 °C

7.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C

8.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

9.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂ / 2.5 h / -78 °C

9.2: 92 percent / CH₂Cl₂ / 3 h / -78 °C

10.1: aq. LiOH / tetrahydrofuran / 0 - 20 °C

11.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

13.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

14.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.17 h / -78 °C

14.2: 81 percent / tetrahydrofuran; toluene / 4 h / -78 °C

15.1: 91 percent / DIBAL-H / diethyl ether; toluene / 1 h / -78 °C

With 2,6-dimethylpyridine; lithium hydroxide; borane-THF; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; hydrogen fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/jo034870l