(3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate

Base Information

• Chemical Name: (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate
• CAS No.: 1333325-30-6
• Molecular Formula: C₃₂H₅₃O₆PSi₂
• Molecular Weight: 620.914

Synonyms:(3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate

Chemical Property of (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate

There total 19 articles about (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate 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: 83.0%

dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate (1333325-48-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate (1333325-30-6)

Guidance literature:

dimethyl ((3S,4S)-4-(2-tert-butyldiphenylsilyloxyethyl)-2-hydroxy-3-methyltetrahydrofuran-2-yl)methylphosphonate; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol202265g

Reference yield:

(S)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)-2-(2-oxoethyl)but-1-yl acetate (1333325-54-4) → (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate (1333325-30-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

7.2: 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; toluene;

DOI:10.1021/ol202265g

Reference yield:

(4S)-4-(2-tert-butyldiphenylsilyloxyethyl)dihydrofuran-2(3H)-one (1333325-47-5) → (3S,4S)-dimethyl (4-(tert-butyldimethylsilyloxy)methyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-oxohexyl)phosphonate (1333325-30-6)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 3 h / -78 °C / Inert atmosphere

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

2.2: 2 h / -78 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

With n-butyllithium; potassium tert-butylate; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;

DOI:10.1021/ol202265g

upstream raw materials:

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

(S)-2-(2-oxo-2-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)ethyl)pent-4-en-1-yl acetate

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

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

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