4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole

Base Information

• Chemical Name: 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole
• CAS No.: 662168-18-5
• Molecular Formula: C₄₅H₄₆N₂O₂Si
• Molecular Weight: 674.958

Synonyms:4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole

Chemical Property of 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole

Chemical Property:

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Technology Process of 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole

There total 2 articles about 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole 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: 39.0%

(2R,5R)-5-[(tert-butyldiphenylsiloxy)methyl]tetrahydrofuran-2-carbaldehyde + [(1-tritylimidazol-4-yl)methyl]triphenylphosphonium chloride → 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-18-5) + 4-{(E)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-17-4)

Guidance literature:

[(1-tritylimidazol-4-yl)methyl]triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.25h;

(2R,5R)-5-[(tert-butyldiphenylsiloxy)methyl]tetrahydrofuran-2-carbaldehyde; In tetrahydrofuran; hexane; at -70 ℃; for 0.5h;

DOI:10.1055/s-2003-42442

Reference yield:

(2R,5R)-5-[(tert-butyldiphenylsiloxy)methyl]tetrahydrofuran-2-carbaldehyde + diethyl (1-tritylimidazol-4-yl)methylphosphonate (473659-21-1) → 4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-18-5) + 4-{(E)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-17-4)

Guidance literature:

With potassium tert-butylate; for 17h; Title compound not separated from byproducts; Heating;

DOI:10.1055/s-2003-42442

Reference yield: 66.0%

4-{(Z)-2-[(2R,5R)-5-tert-butyldiphenylsiloxymethyl-tetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-18-5) → 4-{(Z)-2-[(2R,5R)-5-hydroxymethyltetrahydrofuran-2-yl]vinyl}-1-tritylimidazole (662168-20-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2003-42442

upstream raw materials:

diethyl (1-tritylimidazol-4-yl)methylphosphonate

Downstream raw materials:

4-{(Z)-2-[(2R,5R)-5-hydroxymethyltetrahydrofuran-2-yl]vinyl}-1-tritylimidazole

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