4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

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Chemical Name:4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether
CAS No.:269725-87-3
Molecular Formula:C₃₂H₄₅F₄N₃O₃Si
Molecular Weight:623.807
Hs Code.:

Synonyms:4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

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Chemical Property of 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

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Technology Process of 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

There total 10 articles about 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether 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: 69.0%

: 180293-27-0
4-azido-4-(bromomethyl)-2,3,5,6-tetrafluorobenzene

: 220953-89-9
6-((2R)-6-{[tert-butyl(dimethyl)-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-yl)-1-hexanol

: 269725-87-3
4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

Guidance literature:: 6-((2R)-6-{[tert-butyl(dimethyl)-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-yl)-1-hexanol; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.666667h;

4-azido-4-(bromomethyl)-2,3,5,6-tetrafluorobenzene; In tetrahydrofuran; at 0 - 20 ℃; Further stages.;
DOI:10.1021/jo000029l

Reference yield:

: 34626-52-3
5-hydroxypentyltriphenylphosphonium bromide

: 269725-87-3
4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C

1.2: 86 percent / tetrahydrofuran / 3 h / 20 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h

3.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 0 °C

3.2: 69 percent / tetrahydrofuran / 0 - 20 °C

With potassium tert-butylate; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; 1.1: deprotonation / 1.2: Wittig reaction / 2.1: Hydrogenolysis / 3.1: deprotonation / 3.2: Alkylation;
DOI:10.1021/jo000029l

Reference yield:

: 70897-17-5
(S)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid methyl ester

: 269725-87-3
4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / imidazole / dimethylformamide / 5 h / 85 °C

2.1: 86 percent / DIBAL-H / hexane / 2.5 h / -57 °C

3.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C

3.2: 86 percent / tetrahydrofuran / 3 h / 20 °C

4.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h

5.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 0 °C

5.2: 69 percent / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Reduction / 3.1: deprotonation / 3.2: Wittig reaction / 4.1: Hydrogenolysis / 5.1: deprotonation / 5.2: Alkylation;
DOI:10.1021/jo000029l