(2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 908862-32-8
• Molecular Formula: C₄₂H₇₃NO₄SSi₂
• Molecular Weight: 744.283

Synonyms:

Chemical Property of (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

There total 2 articles about (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl 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:

diethyl 1-cyanomethylphosphonate (2537-48-6) + (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-oxo-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-31-7) → (2Z)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-32-8) + (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-32-8)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 15h;

(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-oxo-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether; In tetrahydrofuran; hexane; at -40 ℃; for 2h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.bmc.2008.05.043

Reference yield:

diethyl 1-cyanomethylphosphonate (2537-48-6) + (20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-oxo-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-31-7) → (2Z)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-32-8) + (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-32-8)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 15h;

(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-oxo-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether; In tetrahydrofuran; hexane; at -40 ℃; for 2h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.bmc.2008.05.043

Reference yield:

(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-cyanomethylene-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-32-8) → (2Z)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-[2-(formyl)ethylidene]-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-33-9) + (2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-[2-(formyl)ethylidene]-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D3 tert-butyldimethylsilyl ether (908862-33-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1.5h; Title compound not separated from byproducts.;

DOI:10.1016/j.bmc.2008.05.043

upstream raw materials:

diethyl 1-cyanomethylphosphonate

(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-oxo-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

Downstream raw materials:

(2Z)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-[2-(formyl)ethylidene]-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

(2E)-(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-[2-(formyl)ethylidene]-22-thia-25-[(methoxymethyl)oxy]-26,27-dimethyl-16-ene-19,24-dinorvitamin D₃ tert-butyldimethylsilyl ether

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