(4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one

Base Information

• Chemical Name: (4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one
• CAS No.: 910818-92-7
• Molecular Formula: C₁₅H₁₄O₅S
• Molecular Weight: 306.339
• Mol file: 910818-92-7.mol

Synonyms:(4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one

Chemical Property of (4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one

There total 1 articles about (4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-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: 95.0%

(4R,5R)-1-furan-2-yl-4,5-dihydroxy-5-phenyl-pentan-1-one (910818-90-5) → (4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one (910818-92-7)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b606874j

Reference yield: 84.0%

(4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one (910818-92-7) → (4R,5S)-1-(furan-2-yl)-5-azido-4-hydroxy-5-phenyl-pentan-1-one (910818-94-9)

Guidance literature:

With sodium azide; water; In N,N-dimethyl-formamide; at 60 ℃; for 46h;

DOI:10.1039/b606874j

Reference yield:

(4'R,5'R)-1-furan-2''-yl-3-(2'-oxo-5'-phenyl-[1',3',2']dioxathiolan-4'-yl)-propan-1-one (910818-92-7) → C25H22NF3O4

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / NaN₃; H₂O / dimethylformamide / 46 h / 60 °C

2: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 23 h

3: 30 percent / LDA / tetrahydrofuran / 21 h / -78 - 20 °C

4: PPh₃ / tetrahydrofuran; H₂O

5: CH₂Cl₂

With dmap; sodium azide; water; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 4: Staudinger reaction;

DOI:10.1039/b606874j

upstream raw materials:

(4R,5R)-1-furan-2-yl-4,5-dihydroxy-5-phenyl-pentan-1-one

Downstream raw materials:

(4R,5S)-1-(furan-2-yl)-5-azido-4-hydroxy-5-phenyl-pentan-1-one

(4R,5S)-1-(furan-2'-yl)-5-azido-4-diphenylphosphinoyloxy-5-phenyl-pentan-1-one

(1'R,2'R,1''R)-{2'-[(1''-azido-1''-phenyl)-methyl]-cyclopropyl}-1-(furan-2'''-yl)-methanone