[6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Base Information

• Chemical Name: [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde
• CAS No.: 881838-57-9
• Molecular Formula: C₅₁H₇₈BrNO₁₀Si
• Molecular Weight: 973.171

Synonyms:

Chemical Property of [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde

There total 16 articles about [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde 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:

2-[6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol → [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde (881838-57-9)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/chem.200500892

Reference yield:

[6-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde → [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde (881838-57-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 181 mg / NaBH₄ / methanol / 0.5 h / 0 °C

2.1: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: HIO₄ / ethyl acetate / 6 h / 0 °C

4.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

5.1: 49 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

6.2: 78 percent / tetrahydrofuran / -78 - 20 °C

7.1: LiNEt₂ / tetrahydrofuran; hexane / 0.17 h / -78 °C

7.2: 61 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C

8.1: 81 percent / PPTS / 12 h / 30 °C

9.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

10.1: 78 percent / NaHMDS / tetrahydrofuran / 0.67 h / -78 °C

11.1: NH₄F / methanol / 3 h / 50 °C

12.1: 71 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; ammonium fluoride; sodium tetrahydroborate; lithium diethylamide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; Dess-Martin periodane; periodic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; 5.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation / 10.1: Julia olefination / 12.1: Dess-Martin oxidation;

DOI:10.1002/chem.200500892

Reference yield:

1-[6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanol → [6-(2-{2-[6-(9-bromo-6-methoxy-3-methyl-1-triisopropylsilanyloxy-nona-2,4,8-trienyl)-2,4-dimethoxy-tetrahydro-pyran-2-ylmethyl]-oxazol-4-yl}-1-methyl-vinyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetaldehyde (881838-57-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 49 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: 78 percent / tetrahydrofuran / -78 - 20 °C

3.1: LiNEt₂ / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 61 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C

4.1: 81 percent / PPTS / 12 h / 30 °C

5.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

6.1: 78 percent / NaHMDS / tetrahydrofuran / 0.67 h / -78 °C

7.1: NH₄F / methanol / 3 h / 50 °C

8.1: 71 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; ammonium fluoride; lithium diethylamide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Dess-Martin oxidation / 5.1: Dess-Martin oxidation / 6.1: Julia olefination / 8.1: Dess-Martin oxidation;

DOI:10.1002/chem.200500892

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(2R,3R,4R,5R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-iodomethyl-3,5-dimethyl-tetrahydro-pyran-4-ol

(2R,3R,4R,5R,6S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-iodomethyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran

[(2R,3S,4S,5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-acetonitrile

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