methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

Base Information

Chemical Name:methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate
CAS No.:215173-37-8
Molecular Formula:C₃₂H₃₄O₇SSi
Molecular Weight:590.769
Hs Code.:

Synonyms:methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

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Chemical Property of methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

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Technology Process of methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

There total 5 articles about methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate 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: 95.0%

: 215173-29-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-3-(5-phenylthio-2-furoyloxy)-2-(tetrahydro-2H-pyran-2-yloxy)butanoate

: 215173-37-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

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

Reference yield:

: 13171-64-7
Dimethyl D-tartrate

: 215173-37-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

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: 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

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

: 215173-37-8
methyl (2S,3R)-4-tert-butyldiphenylsiloxy-2-hydroxy-3-(5-phenylthio-2-furoyloxy)butanoate

Guidance literature:: Multi-step reaction with 3 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

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