1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

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Chemical Name:1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol
CAS No.:623566-56-3
Molecular Formula:C₃₂H₄₈O₃Si
Molecular Weight:508.817
Hs Code.:

Synonyms:1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

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Chemical Property of 1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

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Technology Process of 1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

There total 9 articles about 1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-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: 80.0%

: 502160-04-5
1-{(6R)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydro-pyran-(2S)-yl}-6-methyl-hept-3-en-2-one

: 623566-56-3
1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

Guidance literature:: With dimethylsulfide borane complex; (S)-Corey's chiral borane; In tetrahydrofuran; at -20 ℃; for 8h;
DOI:10.1021/ol035581m

Reference yield:

: methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate

: 623566-56-3
1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / TMSOTf / CH₂Cl₂ / 4 h / -50 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

3.1: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

4.1: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

5.1: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

6.1: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

7.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 0.33 h / -78 °C

7.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 2 h / -78 - 0 °C

8.1: 91 percent / Dess-Martin periodinane / methanol; H₂O; tetrahydrofuran / 20 °C

9.1: 80 percent / (S)-Corey's chiral borane; BH₃*SMe₂ / tetrahydrofuran / 8 h / -20 °C

With 1H-imidazole; peracetic acid; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; (S)-Corey's chiral borane; mercury(II) diacetate; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform-d1; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol035581m

Reference yield:

: 623566-47-2
(2S,5S,6S)-6-[2-(dimethylphenylsilyl)vinyl]-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 623566-56-3
1-{(6S)-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(5S)-methyl-tetrahydropyran-(2S)-yl}-6-methyl-hept-3-en-(2R)-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

2.1: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

3.1: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

4.1: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

5.1: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

6.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 0.33 h / -78 °C

6.2: 97 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 2 h / -78 - 0 °C

7.1: 91 percent / Dess-Martin periodinane / methanol; H₂O; tetrahydrofuran / 20 °C

8.1: 80 percent / (S)-Corey's chiral borane; BH₃*SMe₂ / tetrahydrofuran / 8 h / -20 °C

With 1H-imidazole; peracetic acid; dimethylsulfide borane complex; (S)-Corey's chiral borane; mercury(II) diacetate; methyltriphenoxyphosphonium iodide; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform-d1; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol035581m