methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

Base Information

Chemical Name:methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate
CAS No.:246510-37-2
Molecular Formula:C₂₀H₃₂O₅SSi
Molecular Weight:412.623
Hs Code.:

Synonyms:methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

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Chemical Property of methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

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Technology Process of methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

There total 9 articles about methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate 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: 84.0%

: 246510-36-1
methyl (4S,2R,3R)-4-triethylsiloxy-6-phenylthio-3-methyltetrahydro-2H-pyran-2-carboxylate

: 246510-37-2
methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 ℃; for 0.75h;
DOI:10.1016/S0040-4020(99)00438-X

Reference yield:

: 246510-31-6
(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester

: 246510-37-2
methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / imidazole / CH₂Cl₂ / 0.25 h / 0 °C

2: 1.40 g / triethylsilane / Pd/C / acetone / 0.58 h

3: 71 percent / BF₃*Et₂O / toluene / 0.5 h / -93 °C

4: triethylsilane / Pd/C / acetone / 3 h

5: camphorsulfonic acid / CH₂Cl₂ / 168 h

6: 0.760 g / imidazole / CH₂Cl₂ / 0.08 h / 0 °C

7: 91 percent / ZnI₂ / 1,2-dichloro-ethane / 1.5 h

8: 84 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / ethyl acetate / 0.75 h / 0 °C

With 1H-imidazole; triethylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetone; toluene; 1: Substitution / 2: Reduction / 3: Condensation / 4: Reduction / 5: Cyclization / 6: Substitution / 7: Substitution / 8: Oxidation;
DOI:10.1016/S0040-4020(99)00438-X

Reference yield:

: 246510-33-8
(2R,3S)-3-Methyl-4-oxo-2-triethylsilanyloxy-butyric acid ethyl ester

: 246510-37-2
methyl (4S,2R,3R)-4-triethylsiloxy-6-(phenylsulfinyl)-3-methyltetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / BF₃*Et₂O / toluene / 0.5 h / -93 °C

2: triethylsilane / Pd/C / acetone / 3 h

3: camphorsulfonic acid / CH₂Cl₂ / 168 h

4: 0.760 g / imidazole / CH₂Cl₂ / 0.08 h / 0 °C

5: 91 percent / ZnI₂ / 1,2-dichloro-ethane / 1.5 h

6: 84 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / ethyl acetate / 0.75 h / 0 °C

With 1H-imidazole; triethylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetone; toluene; 1: Condensation / 2: Reduction / 3: Cyclization / 4: Substitution / 5: Substitution / 6: Oxidation;
DOI:10.1016/S0040-4020(99)00438-X