(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester
CAS No.:440641-95-2
Molecular Formula:C₃₀H₄₂O₈Si₂
Molecular Weight:586.83
Hs Code.:

(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

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Technology Process of (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

There total 14 articles about (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester 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:

: 13171-64-7
Dimethyl D-tartrate

: 440641-95-2
(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 62 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 72 h

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

2.2: NaBH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

4.1: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

6.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

7.1: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

8.1: 98 mg / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

9.1: aluminum amalgam; H₂O; 2percent HgCl₂ / tetrahydrofuran / 3 h

With 1H-imidazole; dmap; aluminium amalgam; dimethylsulfide borane complex; water; hydrogen; dimethylaluminum chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 6.1: Dess-Martin oxidation;
DOI:10.1021/jo011157s

Reference yield:

: 93499-95-7,102573-08-0
(2S,3R)-3,4-Dihydroxy-2-(tetrahydro-pyran-2-yloxy)-butyric acid methyl ester

: 440641-95-2
(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

3: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

4: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

5: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

6: 98 mg / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

7: aluminum amalgam; H₂O; 2percent HgCl₂ / tetrahydrofuran / 3 h

With 1H-imidazole; dmap; aluminium amalgam; water; hydrogen; dimethylaluminum chloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 4: Dess-Martin oxidation;
DOI:10.1021/jo011157s

Reference yield:

: 93499-93-5
dimethyl O-tetrahydro-2H-pyran-2-yl-D-tartrate

: 440641-95-2
(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-oxo-4-(3-oxo-butyl)-3-trimethylsilanyloxy-tetrahydro-furan-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

1.2: NaBH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

3.1: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

4.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

5.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 89 percent / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C

7.1: 98 mg / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

8.1: aluminum amalgam; H₂O; 2percent HgCl₂ / tetrahydrofuran / 3 h

With 1H-imidazole; dmap; aluminium amalgam; dimethylsulfide borane complex; water; hydrogen; dimethylaluminum chloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 5.1: Dess-Martin oxidation;
DOI:10.1021/jo011157s