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)-heptyl 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)-heptyl ether
CAS No.:269725-95-3
Molecular Formula:C₃₃H₄₇F₄N₃O₃Si
Molecular Weight:637.834
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)-heptyl 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)-heptyl 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)-heptyl 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)-heptyl 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: 58.0%

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

: 220953-98-0
7-((2R)-6-{[tert-butyl(dimethyl)-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-yl)-1-heptanol

: 269725-95-3
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)-heptyl ether

Guidance literature:: 7-((2R)-6-{[tert-butyl(dimethyl)-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-yl)-1-heptanol; 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:

: 68760-65-6
(6-hydroxyhexyl)triphenylphosphonium bromide

: 269725-95-3
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)-heptyl ether

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 84.5 percent / tetrahydrofuran / 3 h / 20 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h

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

3.2: 58 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

: 269725-95-3
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)-heptyl 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: 84.5 percent / tetrahydrofuran / 3 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h

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

5.2: 58 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