(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Base Information

Chemical Name:(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one
CAS No.:302348-80-7
Molecular Formula:C₁₉H₂₆O₄Si
Molecular Weight:346.499
Hs Code.:

Synonyms:(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

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

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

There total 11 articles about (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-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: 78.0%

: 302348-89-6
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-trans-styryl-5,6-dihydro-pyran-2-one

: 302348-80-7
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 8h;
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

: 302348-80-7
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-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 percent / AIBN; PhSH / benzene / Heating

3: 78 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 8 h / 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; thiophenol; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene; 1: Wittig reaction;
DOI:10.1016/S0040-4020(01)00355-6

Reference yield:

: 302348-87-4
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-hydroxymethyl-5,6-dihydro-pyran-2-one

: 302348-80-7
(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 90 percent / AIBN; PhSH / benzene / Heating

4: 78 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 8 h / 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; Dess-Martin periodane; thiophenol; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene; 1: Dess-Martin oxidation / 2: Wittig reaction;
DOI:10.1016/S0040-4020(01)00355-6