(-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol

Base Information

• Chemical Name: (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol
• CAS No.: 729593-92-4
• Molecular Formula: C₁₈H₁₈O₅S
• Molecular Weight: 346.404
• Mol file: 729593-92-4.mol

Synonyms:(-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol

Chemical Property of (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol

There total 5 articles about (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol 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: 65.0%

(-)-(3R,6S)-6-phenyl-5-(p-tolylsulfonyl)-3,6-dihydro-2H-pyran-3-ol (729593-89-9) → (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol (729593-92-4)

Guidance literature:

With tert.-butylhydroperoxide; sodium hydride; In tetrahydrofuran; at -30 - 20 ℃; for 1.5h;

DOI:10.1021/ol049393n

Reference yield: 24.0%

(-)-(3R,6S)-6-phenyl-5-(p-tolylsulfonyl)-3,6-dihydro-2H-pyran-3-ol (729593-89-9) → (-)-(2S,3S,4S,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol (1045346-28-8) + (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol (729593-92-4)

Guidance literature:

With tert.-butylhydroperoxide; n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 2h;

DOI:10.1021/jo801029q

Reference yield:

(-)-(2S,3R,RS)-2-phenyl-3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran (729593-99-1) → (-)-(2S,3R,4R,5S)-2-phenyl-3-(p-tolylsulfonyl)-3,4-epoxytetrahydro-2H-pyran-5-ol (729593-92-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / OsO₄; Me₃NO

2.1: SOCl₂; Et₃N / 0 °C

2.2: 95 percent / DBU / 20 °C

3.1: t-BuOONa

With osmium(VIII) oxide; thionyl chloride; trimethylamine-N-oxide; sodium tert-butyl hydroperoxide; triethylamine;

DOI:10.1080/10426500590910819

upstream raw materials:

(-)-(3R,6S)-6-phenyl-5-(p-tolylsulfonyl)-3,6-dihydro-2H-pyran-3-ol

(-)-(2S,3R,R_S)-2-phenyl-3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran

(-)-(S)-2-(Z)-4-(Z)-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol

(+)-(3S,4S,5R,6S)-6-phenyl-5-(p-tolylsulfonyl)-tetrahydro-2H-pyran-3,4-diol

Downstream raw materials:

(R)-4,5-dihydroxy-1-phenylpentan-2-one

(2S,5R)-5-hydroxy-2-phenyldihydro-2H-pyran-3(4H)-one

(2S,4S,5S)-4-bromo-5-hydroxy-2-phenyldihydro-2H-pyran-3(4H)-one