(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

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Chemical Name:(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one
CAS No.:302348-88-5
Molecular Formula:C₁₃H₁₂O₄
Molecular Weight:232.236
Hs Code.:

Synonyms:(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

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Chemical Property of (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

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Technology Process of (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

There total 12 articles about (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 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: 80.0%

: 302348-76-1
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

: 302348-88-5
(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)00355-6

Reference yield:

: 302348-75-0
(3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde

: 302348-88-5
(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: n-BuLi; benzyl triphenylphosphonium bromide / tetrahydrofuran / 0.5 h / -78 °C

2: 90 mg / m-CPBA; NaHCO₃ / CH₂Cl₂ / 8 h / 20 °C

3: 80 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1: Wittig reaction;
DOI:10.1016/S0040-4020(01)00355-6

Reference yield:

: 302348-72-7
(6S)-6-tert-butyldimethylsilanyloxymethyl-(5S)-5-hydroxy-5,6-dihydro-pyran-2-one

: 302348-88-5
(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / CH₂Cl₂; various solvent(s) / 0.5 h / 0 °C

2: 91 percent / 5 percent aq. HF / acetonitrile / 6 h / 20 °C

3: 80 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4: n-BuLi; benzyl triphenylphosphonium bromide / tetrahydrofuran / 0.5 h / -78 °C

5: 90 mg / m-CPBA; NaHCO₃ / CH₂Cl₂ / 8 h / 20 °C

6: 80 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; 3: Dess-Martin oxidation / 4: Wittig reaction;
DOI:10.1016/S0040-4020(01)00355-6