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

Base Information

Chemical Name:(20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether
CAS No.:1335097-70-5
Molecular Formula:C₄₇H₉₀O₃Si₃
Molecular Weight:787.486
Hs Code.:

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

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

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

There total 15 articles about (20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-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: 78.0%

: 1335097-69-2
(20R)-des-A,B-22,22-dimethyl-25-[(triethylsilyl)oxy]cholestan-8-one

: 213250-64-7
[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

: 1335097-70-5
(20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

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

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

Reference yield:

: 1335097-65-8
(8S,20R)-des-A,B-20-(1',1'-dimethyl-2'-oxo-ethyl)-8-[(triethylsilyl)oxy]pregnane

: 1335097-70-5
(20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -10 °C

1.2: 22 h / -10 - 37 °C / Inert atmosphere

2.1: hydrogen / palladium 10% on activated carbon / methanol / 20 h / 20 °C

3.1: diethyl ether / 20 h / 0 - 20 °C

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

5.1: 2,6-dimethylpyridine / dichloromethane / -50 - -40 °C

6.1: phenyllithium / tetrahydrofuran; di-n-buthyl ether / 0.5 h / -30 °C

6.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; tetrapropylammonium perruthennate; hydrogen; phenyllithium; 4-methylmorpholine N-oxide; diisopropylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; di-n-buthyl ether;

Reference yield:

: (8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-allyl)-8β-[(triethylsilyl)oxy]pregnane

: 1335097-70-5
(20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrogen / palladium 10% on activated carbon / methanol / 20 h / 20 °C

2.1: diethyl ether / 20 h / 0 - 20 °C

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

4.1: 2,6-dimethylpyridine / dichloromethane / -50 - -40 °C

5.1: phenyllithium / tetrahydrofuran; di-n-buthyl ether / 0.5 h / -30 °C

5.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrapropylammonium perruthennate; hydrogen; phenyllithium; 4-methylmorpholine N-oxide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; di-n-buthyl ether;