(S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate

Base Information

• Chemical Name: (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate
• CAS No.: 1431611-10-7
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.331
• Mol file: 1431611-10-7.mol

Synonyms:(S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate

Chemical Property of (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate

There total 4 articles about (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate 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: 89.0%

(S)-tert-butyl (5-iodo-6-oxo-3,6-dihydro-2H-pyran-3-yl)carbamate (1431611-05-0) + tributylphenylstannane (960-16-7) → (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate (1431611-10-7)

Guidance literature:

With dichlorobis(tri-O-tolylphosphine)palladium; zinc dibromide; In N,N-dimethyl-formamide; at 20 - 65 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jm400346a

Reference yield:

(4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate (126587-36-8) → (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate (1431611-10-7)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C

2: iodine; pyridine / tetrachloromethane / 0.5 h / 20 - 40 °C

3: zinc dibromide; dichlorobis(tri-O-tolylphosphine)palladium / N,N-dimethyl-formamide / 1.5 h / 20 - 65 °C / Inert atmosphere

With pyridine; dichlorobis(tri-O-tolylphosphine)palladium; iodine; trifluoroacetic acid; zinc dibromide; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm400346a

Reference yield:

(2Z,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-penten-5-olide (124085-71-8) → (S)-tert-butyl (6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl)carbamate (1431611-10-7)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; pyridine / tetrachloromethane / 0.5 h / 20 - 40 °C

2: zinc dibromide; dichlorobis(tri-O-tolylphosphine)palladium / N,N-dimethyl-formamide / 1.5 h / 20 - 65 °C / Inert atmosphere

With pyridine; dichlorobis(tri-O-tolylphosphine)palladium; iodine; zinc dibromide; In tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm400346a

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate

(2Z,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-penten-5-olide

(S)-tert-butyl (5-iodo-6-oxo-3,6-dihydro-2H-pyran-3-yl)carbamate

Downstream raw materials:

tert-butyl N-[(tert-butoxy)carbonyl]-N-[(3S)-6-oxo-5-phenyl-3,6-dihydro-2H-pyran-3-yl]carbamate