dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

Base Information

Chemical Name:dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate
CAS No.:1333325-48-6
Molecular Formula:C₂₆H₃₉O₆PSi
Molecular Weight:506.651
Hs Code.:

Synonyms:dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

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Chemical Property of dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

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Technology Process of dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

There total 18 articles about dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate 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: 69.0%

: 1141365-67-4
(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone

: 756-79-6
dimethyl methane phosphonate

: 1333325-48-6
dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

Guidance literature:: dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol202265g

Reference yield:

: 1333325-54-4
(S)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)-2-(2-oxoethyl)but-1-yl acetate

: 1333325-48-6
dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

4.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol202265g

Reference yield:

: 1333325-55-5
(S)-2-(2-hydroxyethyl)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-1-yl acetate

: 1333325-48-6
dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

3.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 3 h / -78 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

5.2: 2 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol202265g