(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

Base Information

Chemical Name:(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran
CAS No.:474126-20-0
Molecular Formula:C₂₃H₃₆O₄Si
Molecular Weight:404.622
Hs Code.:

Synonyms:(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

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Chemical Property of (2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

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Technology Process of (2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

There total 5 articles about (2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 474126-19-7
(2S,3S,6S)-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran-3-ol

: 474126-20-0
(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 8h;
DOI:10.1016/S0040-4020(02)00791-3

Reference yield:

: 129694-45-7
(2S)-6-Hydroxy-2-<(E)-styryl>-6H-pyran-3(2H)-one

: 474126-20-0
(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / pyridinium toluene-p-sulphonate / CH₂Cl₂ / 3 h / 25 °C

2: 78 percent / NaBH₄; CeCl₃*7H₂O / methanol / -40 - 20 °C

3: 2.8 g / Ph₃P; DEAD / tetrahydrofuran / 0 - 20 °C

4: 82 percent / K₂CO₃ / methanol / 10 h / 20 °C

5: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 3: Mitsunobu reaction;
DOI:10.1016/S0040-4020(02)00791-3

Reference yield:

: 129694-46-8
(2S,6S)-6-(1-Ethoxyethoxy)-2-<(E)-styryl>-6H-pyran-3(2H)-one

: 474126-20-0
(2S,3S,6S)-3-tert-butyldimethylsilanyloxy-6-(1-ethoxyethoxy)-2-[(E)-styryl]-3,6-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / NaBH₄; CeCl₃*7H₂O / methanol / -40 - 20 °C

2: 2.8 g / Ph₃P; DEAD / tetrahydrofuran / 0 - 20 °C

3: 82 percent / K₂CO₃ / methanol / 10 h / 20 °C

4: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 2: Mitsunobu reaction;
DOI:10.1016/S0040-4020(02)00791-3