Technology Process of ((1R,2E,4E,6R,8E)-9-bromo-1-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-6-methoxy-3-methylnona-2,4,8-trienyloxy)(tertbutyl)diphenylsilane
There total 23 articles about ((1R,2E,4E,6R,8E)-9-bromo-1-((2R,4R,6R)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-6-methoxy-3-methylnona-2,4,8-trienyloxy)(tertbutyl)diphenylsilane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
chromium dichloride;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 12h;
DOI:10.1039/c2ob25766a
- Guidance literature:
-
Multi-step reaction with 14 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
9.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C
10.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C
10.2: 1.5 h / -10 - 20 °C
11.1: (+)-B-methoxydiisocamphenylborane / diethyl ether / 1 h / 0 - 20 °C
11.2: 1 h / -78 - -15 °C
12.1: sodium hydride / hexane; tetrahydrofuran / 1 h / Reflux
12.2: 1.5 h / Reflux
13.1: osmium(VIII) oxide; sodium periodate / tetrahydrofuran; water / 20 h / 20 °C / Inert atmosphere
14.1: chromium dichloride / tetrahydrofuran / 12 h / 0 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; (+)-B-methoxydiisocamphenylborane;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
4.2: |Swern Oxidation / 7.2: |Swern Oxidation / 8.2: |Horner-Wadsworth-Emmons Olefination / 10.2: |Swern Oxidation / 14.1: |Takai-Utimoto Olefination;
DOI:10.1039/c2ob25766a
- Guidance literature:
-
Multi-step reaction with 13 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 5.5 h / 0 - 20 °C
2.1: pyridinium p-toluenesulfonate / methanol / 3 h / Reflux
3.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C
3.2: 1.5 h / -10 - 20 °C
4.1: toluene / 12 h / 100 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C
6.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C
6.2: 1.5 h / -10 - 20 °C
7.1: sodium hydride / hexane; tetrahydrofuran / 0.5 h / 0 °C
7.2: 1 h / 20 °C
8.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C
9.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -78 °C
9.2: 1.5 h / -10 - 20 °C
10.1: (+)-B-methoxydiisocamphenylborane / diethyl ether / 1 h / 0 - 20 °C
10.2: 1 h / -78 - -15 °C
11.1: sodium hydride / hexane; tetrahydrofuran / 1 h / Reflux
11.2: 1.5 h / Reflux
12.1: osmium(VIII) oxide; sodium periodate / tetrahydrofuran; water / 20 h / 20 °C / Inert atmosphere
13.1: chromium dichloride / tetrahydrofuran / 12 h / 0 - 20 °C
With
2,6-dimethylpyridine; chromium dichloride; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; (+)-B-methoxydiisocamphenylborane;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
3.2: |Swern Oxidation / 6.2: |Swern Oxidation / 7.2: |Horner-Wadsworth-Emmons Olefination / 9.2: |Swern Oxidation / 13.1: |Takai-Utimoto Olefination;
DOI:10.1039/c2ob25766a
