(3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Base Information

• Chemical Name: (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• CAS No.: 112741-56-7
• Molecular Formula: C₃₃H₂₉NO₆
• Molecular Weight: 535.596
• Mol file: 112741-56-7.mol

Synonyms:(3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Chemical Property of (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 5 articles about (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-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:

trimethylsilyl enol ether of 4-methoxyacetophenone (220474-37-3) + (3S,5S,6R)-4-(benzyloxycarbonyl)-3-bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (111934-06-6) → (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (112741-56-7) + (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (112741-55-6)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; acetonitrile; at 25 ℃; for 4h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00213a031

Reference yield:

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) → (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (112741-56-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 84.3 percent / triethylamine / tetrahydrofuran / 18 h

2: 9.6 g / NaHCO₃ / CH₂Cl₂; H₂O / 12 h

3: 77.9 percent / p-toluenesulfonic acid monohydrate, CaCl₂ / benzene / 8 h / Heating

4: 100 percent / N-bromosuccinimide / CCl₄ / 0.75 h / Heating

5: ZnCl₂ / acetonitrile; tetrahydrofuran / 4 h / 25 °C

With N-Bromosuccinimide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; calcium chloride; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/ja00213a031

Reference yield:

(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-54-9,335159-14-3) → (3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (112741-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / N-bromosuccinimide / CCl₄ / 0.75 h / Heating

2: ZnCl₂ / acetonitrile; tetrahydrofuran / 4 h / 25 °C

With N-Bromosuccinimide; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; acetonitrile;

DOI:10.1021/ja00213a031

upstream raw materials:

trimethylsilyl enol ether of 4-methoxyacetophenone

(3S,5S,6R)-4-(benzyloxycarbonyl)-3-bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(1R,2S)-2-Amino-1,2-diphenylethanol

(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one