1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

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Chemical Name:1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether
CAS No.:561017-68-3
Molecular Formula:C₄₂H₇₆O₄Si₂
Molecular Weight:701.234
Hs Code.:

Synonyms:1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

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Chemical Property of 1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

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Technology Process of 1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

There total 13 articles about 1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin 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: 93.0%

: 81522-68-1
[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

: 561017-62-7
25-methoxymethyloxy-12-methylene-de-A,B-cholestan-8-one

: 561017-68-3
1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

Guidance literature:: [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

25-methoxymethyloxy-12-methylene-de-A,B-cholestan-8-one; In tetrahydrofuran; at -78 - -40 ℃; for 5h;
DOI:10.1021/ol034632c

Reference yield:

: 139619-76-4
(1R,3aR,7aR)-1-((R)-5-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-1,2,3,3a,7,7a-hexahydro-inden-4-one

: 561017-68-3
1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 13 steps

1.1: 94 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: 99 percent / imidazole / dimethylformamide / 20 °C

3.1: 94 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 5 h / 0 - 20 °C

4.1: 97 percent / lithium diethylamide; HMPA / diethyl ether; hexane / 20 °C

5.1: 99 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 20 °C

6.1: 99 percent / triethylamine / CH₂Cl₂ / 3 h

7.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 20 °C

8.1: 95 percent / H₂ / 5 percent Pd/C / ethyl acetate / 2 h / 20 °C

9.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 24 h / 20 °C

10.1: potassium tert-butoxide / toluene / 0.5 h / 90 °C

10.2: 98 percent / toluene / 3 h / 90 °C

11.1: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 24 h / Heating

12.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 6 h / 20 °C

13.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

13.2: 93 percent / tetrahydrofuran / 5 h / -78 - -40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; n-butyllithium; potassium tert-butylate; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; sodium naphthalenide; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 10.2: Wittig reaction / 13.2: Wittig-Horner reaction;
DOI:10.1021/ol034632c

Reference yield:

: 561017-43-4
25-methoxymethyloxy-de-A,B-cholest-9(11)-en-8β-ol

: 561017-68-3
1α-tert-butyldimethylsilyloxy-25-methoxymethyloxy-12-methylene-vitamin D3 tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / imidazole / dimethylformamide / 20 °C

2.1: 94 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 5 h / 0 - 20 °C

3.1: 97 percent / lithium diethylamide; HMPA / diethyl ether; hexane / 20 °C

4.1: 99 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 20 °C

5.1: 99 percent / triethylamine / CH₂Cl₂ / 3 h

6.1: 89 percent / sodium naphthalenide / tetrahydrofuran / 20 °C

7.1: 95 percent / H₂ / 5 percent Pd/C / ethyl acetate / 2 h / 20 °C

8.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 24 h / 20 °C

9.1: potassium tert-butoxide / toluene / 0.5 h / 90 °C

9.2: 98 percent / toluene / 3 h / 90 °C

10.1: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 24 h / Heating

11.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 6 h / 20 °C

12.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

12.2: 93 percent / tetrahydrofuran / 5 h / -78 - -40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; n-butyllithium; potassium tert-butylate; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; sodium naphthalenide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 9.2: Wittig reaction / 12.2: Wittig-Horner reaction;
DOI:10.1021/ol034632c