2H-Pyran-3-ol, 3,6-dihydro-6-phenyl-, (3S,6R)-

Base Information

• Chemical Name: 2H-Pyran-3-ol, 3,6-dihydro-6-phenyl-, (3S,6R)-
• CAS No.: 729593-82-2
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Mol file: 729593-82-2.mol

Synonyms:

Chemical Property of 2H-Pyran-3-ol, 3,6-dihydro-6-phenyl-, (3S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-3-ol, 3,6-dihydro-6-phenyl-, (3S,6R)-

There total 2 articles about 2H-Pyran-3-ol, 3,6-dihydro-6-phenyl-, (3S,6R)- 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: 92.0%

(-)-(2S,3R,RS)-2-phenyl-3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran (729593-99-1) → (+)-(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-ol (729593-82-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 70 ℃; Inert atmosphere;

DOI:10.1021/jo8015709

Reference yield:

(-)-(S)-2-(Z)-4-(Z)-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol (729593-95-7) → (+)-(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-ol (729593-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran / -78 - 20 °C

2: 50 percent / P(OMe)3 / methanol / 96 h / 50 °C

With lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol;

DOI:10.1080/10426500590910819

Reference yield: 62.0%

propynoic acid methyl ester (922-67-8) + (+)-(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-ol (729593-82-2) → methyl (+)-(E)-3-[(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-yloxy]acrylate (1173009-10-3)

Guidance literature:

propynoic acid methyl ester; With triethylamine; In diethyl ether; at 0 ℃; for 0.333333h; Inert atmosphere;

(+)-(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-ol; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 19h;

DOI:10.1002/ejoc.200801133

upstream raw materials:

(-)-(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

Downstream raw materials:

methyl (+)-(E)-3-[(3S,6R)-6-phenyl-3,6-dihydro-2H-pyran-3-yloxy]acrylate