methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

Base Information

Chemical Name:methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate
CAS No.:440640-98-2
Molecular Formula:C₂₇H₃₀O₈Si
Molecular Weight:510.616
Hs Code.:

Synonyms:methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

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Chemical Property of methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

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Technology Process of methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

There total 6 articles about methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate 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: 97.0%

: 440641-83-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-methoxy-2-furoyloxy)butanoate

: 440640-98-2
methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1021/jo011157s

Reference yield:

: 13171-64-7
Dimethyl D-tartrate

: 440640-98-2
methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

Guidance literature:: Multi-step reaction with 6 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: 83 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 20 °C

5.1: 96 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

6.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; dmap; dimethylsulfide borane complex; dimethylaluminum chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 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

: 440640-98-2
methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-methoxy-2-furoyloxy)-2-oxobutanoate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 83 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3: 96 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

4: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; dmap; dimethylaluminum chloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In dichloromethane; 4: Dess-Martin oxidation;
DOI:10.1021/jo011157s