(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

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Chemical Name:(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate
CAS No.:1407517-31-0
Molecular Formula:C₃₂H₄₄O₆Si
Molecular Weight:552.783
Hs Code.:

Synonyms:(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

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Chemical Property of (R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

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Technology Process of (R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

There total 17 articles about (R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate 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: 96.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 1407517-30-9
(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

: 1407517-31-0
(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal; In tetrahydrofuran; hexane; at 20 ℃; for 1h;
DOI:10.1039/c2ob25766a

Reference yield:

: 920018-58-2
(R)-1-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)ethane-1,2-diol

: 1407517-31-0
(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 12 h

2.1: 2,6-dimethylpyridine / dichloromethane / 5.5 h / 0 - 20 °C

3.1: pyridinium p-toluenesulfonate / methanol / 3 h / Reflux

4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C

4.2: 1.5 h / -10 - 20 °C

5.1: toluene / 12 h / 100 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

7.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C

7.2: 1.5 h / -10 - 20 °C

8.1: sodium hydride / hexane; tetrahydrofuran / 0.5 h / 0 °C

8.2: 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 4.2: |Swern Oxidation / 7.2: |Swern Oxidation / 8.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c2ob25766a

Reference yield:

: 73346-73-3
(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

: 1407517-31-0
(R,2E,4E)-ethyl 6-(tert-butyldiphenylsilanyloxy)-6-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-methylhexa-2,4-dienoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 24 h / Reflux

2.1: sodium hydride / hexane; tetrahydrofuran / 0.75 h

2.2: 10 h

3.1: pyridine / 16 h / 0 °C

4.1: sodium iodide / acetone / 30 h / Reflux

5.1: dimethyl sulfoxide / 72 h / 20 °C

6.1: diisobutylaluminium hydride / diethyl ether / 2 h / -78 °C

7.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether; hexane / 1 h / 0 - 20 °C

7.2: 1 h / -78 - 0 °C

8.1: ozone; triphenylphosphine / dichloromethane / 0.5 h / -78 - 20 °C

9.1: pyridinium p-toluenesulfonate / methanol / 12 h / Reflux

10.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 12 h

11.1: 2,6-dimethylpyridine / dichloromethane / 5.5 h / 0 - 20 °C

12.1: pyridinium p-toluenesulfonate / methanol / 3 h / Reflux

13.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C

13.2: 1.5 h / -10 - 20 °C

14.1: toluene / 12 h / 100 °C / Inert atmosphere

15.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

16.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C

16.2: 1.5 h / -10 - 20 °C

17.1: sodium hydride / hexane; tetrahydrofuran / 0.5 h / 0 °C

17.2: 1 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 4.1: |Finkelstein Reaction / 13.2: |Swern Oxidation / 16.2: |Swern Oxidation / 17.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c2ob25766a