(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

Base Information

Chemical Name:(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one
CAS No.:860267-79-4
Molecular Formula:C₅₇H₉₂O₁₀Si
Molecular Weight:965.437
Hs Code.:

Synonyms:(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

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Chemical Property of (5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

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Technology Process of (5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

There total 5 articles about (5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one 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:

: [(3R,6R)-3,6-Bis-methoxymethoxy-6-((2R,5R,6R)-5-methoxymethoxy-6-tetradecyl-tetrahydro-pyran-2-yl)-hexyl]-triphenyl-phosphonium; iodide

: 198541-55-8
(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

: 860267-79-4
(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

Guidance literature:: [(3R,6R)-3,6-Bis-methoxymethoxy-6-((2R,5R,6R)-5-methoxymethoxy-6-tetradecyl-tetrahydro-pyran-2-yl)-hexyl]-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal; In tetrahydrofuran; at -78 ℃; for 1.2h;
DOI:10.1021/ol0508126

Reference yield:

: (7R,8R,11R,12R)-8,12-oxido-7,11-di(methoxymethoxy)-1-hexacosen-4-ol

: 860267-79-4
(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N-diisopropylethylamine / 1,2-dichloro-ethane / 3 h / 50 °C

2.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

2.2: NaBH₄ / CH₂Cl₂; ethanol / -78 - 20 °C

3.1: iodine; imidazole; triphenylphosphine / benzene / 2.5 h / 5 - 20 °C

4.1: acetonitrile / 168 h / 60 °C

5.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 - 0 °C

5.2: 43 percent Turnov_. / tetrahydrofuran / 1.2 h / -78 °C

With 1H-imidazole; iodine; sodium hexamethyldisilazane; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetonitrile; benzene; 5.2: Wittig reaction;
DOI:10.1021/ol0508126

Reference yield:

: (3R,6R,7R,10R,11R)-1-iodo-7,11-oxido-3,6,10-tri(methoxymethoxy)-pentacosane

: 860267-79-4
(5S)-3-[(2R,8R,11R,12R,15R,16R)-2-(tert-butyldiphenylsilanyloxy)-8,11,15-tri(methoxymethoxy)-12,16-oxido-triacont-5-enyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetonitrile / 168 h / 60 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 - 0 °C

2.2: 43 percent Turnov_. / tetrahydrofuran / 1.2 h / -78 °C

With sodium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 2.2: Wittig reaction;
DOI:10.1021/ol0508126