methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

Base Information

Chemical Name:methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate
CAS No.:440641-85-0
Molecular Formula:C₃₃H₃₆O₈Si
Molecular Weight:588.73
Hs Code.:

Synonyms:methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

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Chemical Property of methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

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Technology Process of methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

There total 5 articles about methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate 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: 88.0%

: 440641-78-1
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)butanoate

: 440641-85-0
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

Guidance literature:: With dimethylaluminum chloride; In dichloromethane; at -25 - 20 ℃; for 4h;
DOI:10.1021/jo011157s

Reference yield:

: 13171-64-7
Dimethyl D-tartrate

: 440641-85-0
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

Guidance literature:: Multi-step reaction with 5 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: 87 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 20 °C

5.1: 88 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

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

: 440641-85-0
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-(4-methylphenoxy)-2-furoyloxy)-2-hydroxybutanoate

Guidance literature:: Multi-step reaction with 3 steps

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

2: 87 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3: 88 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

With 1H-imidazole; dmap; dimethylaluminum chloride; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/jo011157s