3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

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Chemical Name:3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3
CAS No.:1181662-14-5
Molecular Formula:C₄₃H₈₀O₆Si₂
Molecular Weight:749.276
Hs Code.:

Synonyms:3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

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Chemical Property of 3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

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Technology Process of 3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

There total 12 articles about 3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3 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: 13.0%

: 1181661-92-6
(1S,6R,7R,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]nonan-2-one

: 145554-08-1
(1R,3S)-1,3-bis((tert-butyl)dimethylsilanyloxy)-5-[2-(diphenylphosphinoyl)ethylene]-4-methylenecyclohexane

: 1305339-99-4
(6R,7R)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-9-en-2-one

: 1181662-14-5
3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: (1R,3S)-1,3-bis((tert-butyl)dimethylsilanyloxy)-5-[2-(diphenylphosphinoyl)ethylene]-4-methylenecyclohexane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

(1S,6R,7R,9S)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]nonan-2-one; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol200828s

Reference yield:

: 1181662-09-8
(1S,5S,6S,7S)-5-[(tert-butyldimethylsilyl)oxy]-9-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-1-methylbicyclo[4.3.0]non-8-en-7-ol

: 1305339-99-4
(6R,7R)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-9-en-2-one

: 1181662-14-5
3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: Multi-step reaction with 5 steps

1.1: palladium on carbon; hydrogen / methanol / 23 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 0 - 80 °C / Inert atmosphere

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; palladium on carbon; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol200828s

Reference yield:

: 1181661-97-1
(1R,2S,6S)-2-[(tert-butyldimethylsilyl)oxy]-6-methylbicyclo[4.3.0]non-8-en-7-one

: 1305339-99-4
(6R,7R)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-9-en-2-one

: 1181662-14-5
3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: Multi-step reaction with 10 steps

1.1: diisobutylaluminium hydride / toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

4.2: 24 h / 0 °C / Inert atmosphere

5.1: magnesium / tetrahydrofuran; diethyl ether / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C

5.3: 20 h / -78 - 20 °C / Inert atmosphere

6.1: palladium on carbon; hydrogen / methanol / 23 h / 20 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 0 - 80 °C / Inert atmosphere

9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

10.2: 3 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; palladium on carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; magnesium; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 4.1: Wittig reaction / 4.2: Wittig reaction;
DOI:10.1021/ol200828s