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

Base Information

• Chemical Name: (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one
• CAS No.: 302348-81-8
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.236
• Mol file: 302348-81-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (5S)-5-hydroxy-(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: 80.0%

(5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-80-7) → (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-81-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)00355-6

Reference yield: 40.0%

(5S,6S)-5-hydroxy-6-[(E)-styryl]-5,6-dihydro-2H-pyran-2-one (160699-77-4) → (+)-7,8-di-epi-altholactone (124868-11-7,65408-91-5,114488-17-4,114488-19-6,120019-23-0,120019-27-4,124868-12-8) + (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-81-8)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(01)00355-6

Reference yield:

(3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde (302348-75-0) → (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-81-8)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 90 percent / AIBN; PhSH / benzene / Heating

3: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

4: 40 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; benzyltriphenylphosphonium bromide; sodium hydrogencarbonate; thiophenol; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene; 1: Wittig reaction;

DOI:10.1016/S0040-4020(01)00355-6

upstream raw materials:

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

(5S,6S)-5-hydroxy-6-[(E)-styryl]-5,6-dihydro-2H-pyran-2-one

(3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde

(S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol

Downstream raw materials:

(+)-7,8-di-epi-altholactone