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

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Chemical Name:16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3
CAS No.:1305340-02-6
Molecular Formula:C₄₃H₇₈O₆Si₂
Molecular Weight:747.26
Hs Code.:

Synonyms:16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

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Chemical Property of 16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

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Technology Process of 16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

There total 12 articles about 16-ene-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: 60.0%

: (1R,6S,9S)-2-(bromomethylene)-9-(methoxymethoxy)-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4.3.0]non-7-ene

: 161055-41-0
(3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne

: 1305340-02-6
16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; at 80 ℃; for 3.5h; Inert atmosphere;
DOI:10.1021/ol200828s

Reference yield:

: 1181662-05-4
(1S,2S,6S,7Z,8S,9R)-2-[(tert-butyldimethylsilyl)oxy]-8,9-epoxy-7-ethylidene-6-methylbicyclo[4.3.0]nonane

: 1305340-02-6
16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 1 h / -78 °C

1.3: 20 h / -78 - 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 80 °C / Inert atmosphere

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / toluene / 3.5 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; magnesium; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol200828s

Reference yield:

: 1305339-95-0
(1S,2S,6S,7R,8S,9R)-2-[(tert-butyldimethylsilyl)oxy]-8,9-epoxy-6-methylbicyclo[4.3.0]nonan-7-ol

: 1305340-02-6
16-ene-3-O-(tert-butyldimethylsilyl)-1α-[(tert-butyldimethylsilyl)oxy]-15α,25-bis(methoxymethoxy)vitamin D3

Guidance literature:: Multi-step reaction with 8 steps

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

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

2.2: 24 h / 0 °C / Inert atmosphere

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

3.2: 1 h / -78 °C

3.3: 20 h / -78 - 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 80 °C / Inert atmosphere

6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

7.2: 3 h / 0 - 20 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / toluene / 3.5 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; magnesium; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 2.1: Wittig reaction / 2.2: Wittig reaction;
DOI:10.1021/ol200828s