(20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether
• CAS No.: 1335097-50-1
• Molecular Formula: C₄₆H₈₈O₃Si₃
• Molecular Weight: 773.459
• Mol file: 1335097-50-1.mol

Synonyms:(20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

Chemical Property of (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

There total 6 articles about (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) 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: 91.0%

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (213250-64-7) + (20R,22R)-des-A,B-22-methyl-25-[(triethylsilyl)oxy]cholestan-8-one (386743-51-7) → (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether (1335097-50-1)

Guidance literature:

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With phenyllithium; In tetrahydrofuran; dibutyl ether; at -30 ℃; for 0.5h;

(20R,22R)-des-A,B-22-methyl-25-[(triethylsilyl)oxy]cholestan-8-one; In tetrahydrofuran; dibutyl ether; at -78 - 4 ℃; for 23h; Inert atmosphere;

Reference yield:

(8S,20R)-des-A,B-22-methyl-8β,25-bis[(triethylsilyl)oxy]cholestane (1335097-38-5) → (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether (1335097-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 4 °C

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

3.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -40 °C

4.1: phenyllithium / dibutyl ether; tetrahydrofuran / 0.5 h / -30 °C

4.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; dibutyl ether; 4.1: Wittig-Horner condensation;

Reference yield:

(8S,20R,22R)-des-A,B-22-methylcholestane-8β,25-diol (1335097-40-9) → (20R,22R)-1α-[(tert-butyldimethylsilyl)oxy]-22-methyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether (1335097-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

2.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -40 °C

3.1: phenyllithium / dibutyl ether; tetrahydrofuran / 0.5 h / -30 °C

3.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrapropylammonium perruthennate; phenyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; dibutyl ether; 3.1: Wittig-Horner condensation;

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(20R,22R)-des-A,B-22-methyl-25-[(triethylsilyl)oxy]cholestan-8-one

(8S,20R)-des-A,B-22-methyl-8β,25-bis[(triethylsilyl)oxy]cholestane

Downstream raw materials:

(20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D₃