(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

Base Information

• Chemical Name: (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal
• CAS No.: 478490-93-6
• Molecular Formula: C₂₈H₄₂O₅Si
• Molecular Weight: 486.724
• Mol file: 478490-93-6.mol

Synonyms:(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

Chemical Property of (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

There total 42 articles about (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal 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: 100.0%

(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol (464914-19-0) → (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal (478490-93-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ja028019k

Reference yield:

(2E,5Z)-(S)-1-{(4S,5S)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-diene-1,7-diol → (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal (478490-93-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / PdCl₂(CH₃CN)2 / tetrahydrofuran / 3 h / 0 °C

2: 89 percent / HCl / methanol / 20 °C

3: 87 percent / DDQ / CH₂Cl₂ / 0 °C

4: 90 percent / imidazole / dimethylformamide / 20 °C

5: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 96 percent / Dess-Martin periodinane

7: 92 percent / benzene / 20 °C

8: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9: 94 percent / Dess-Martin periodinane

With 1H-imidazole; hydrogenchloride; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 6: Dess-Martin oxidation / 7: Wittig reaction / 9: Dess-Martin oxidation;

DOI:10.1002/anie.200500029

Reference yield:

Carbonic acid (2E,5Z)-(S)-7-hydroxy-1-{(4R,5S)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-dienyl ester methyl ester → (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal (478490-93-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 59 percent / neocuproine / Pd₂(dba)3 / toluene / 80 °C

2: 89 percent / HCl / methanol / 20 °C

3: 87 percent / DDQ / CH₂Cl₂ / 0 °C

4: 90 percent / imidazole / dimethylformamide / 20 °C

5: 83 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 96 percent / Dess-Martin periodinane

7: 92 percent / benzene / 20 °C

8: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9: 94 percent / Dess-Martin periodinane

With 1H-imidazole; hydrogenchloride; 2.9-dimethyl-1,10-phenanthroline; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6: Dess-Martin oxidation / 7: Wittig reaction / 9: Dess-Martin oxidation;

DOI:10.1002/anie.200500029

upstream raw materials:

(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol

(E)-(S)-1-[(S)-2-(4-Methoxy-phenyl)-[1,3]dioxan-4-yl]-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-prop-2-en-1-ol

(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal

tert-Butyl-[(E)-(S)-1-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyloxy]-dimethyl-silane

Downstream raw materials:

11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-1-(3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dien-6-ol

4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-yn-1-ol

2-(3-{6-[4-(tert-butoxy-diphenyl-silanyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-one