(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

Base Information

Chemical Name:(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol
CAS No.:223693-17-2
Molecular Formula:C₄₀H₆₂O₅Si₂
Molecular Weight:679.1
Hs Code.:

Synonyms:(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

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Chemical Property of (2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

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Technology Process of (2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

There total 12 articles about (2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-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: 79.0%

: 223693-02-5
(2R,4R,6S)-7-(tert-butyldiphenylsiloxy)-4-[(p-methoxybenzyl)oxy]-2,5,5-trimethyl-6-(triethoxy)heptyl pivalate

: 223693-17-2
(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -30 ℃;
DOI:10.1021/ja990384x

Reference yield:

: 223693-00-3
(2R,4R)-5-formyl-4-[(p-methoxybenzyl)oxy]-2,5-dimethylhexyl pivalate

: 223693-17-2
(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C

1.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C

2.1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

3.1: 636 mg / imidazole / tetrahydrofuran / 5 h

4.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

5.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Metallation / 1.2: Wittig olefination / 2.1: hydroxylation / 3.1: silylation / 4.1: silylation / 5.1: reductive deacylation;
DOI:10.1021/ja993487o

Reference yield:

: 223693-16-1
(2R,4R)-[(p-methoxybenzyl)oxy]-2,5,5-trimethyl-6-heptenyl pivalate

: 223693-17-2
(2R,4R,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2,5,5-trimethyl-6-triethylsilanyloxy-heptan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

2: 636 mg / imidazole / tetrahydrofuran / 5 h

3: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

4: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); diisobutylaluminium hydride; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: hydroxylation / 2: silylation / 3: silylation / 4: reductive deacylation;
DOI:10.1021/ja993487o