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

Base Information

• Chemical Name: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• CAS No.: 135560-80-4
• Molecular Formula: C₂₈H₂₇NO₄
• Molecular Weight: 441.527
• Mol file: 135560-80-4.mol

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

Chemical Property of (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-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 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 1 articles about (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-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: 48.5%

4-iodobut-1-ene (7766-51-0) + (5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-54-9,335159-14-3) → (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (135560-80-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 10 min, 2.) 1 h;

DOI:10.1021/ja00018a040

Reference yield: 88.5%

bromethyl methyl ether (13057-17-5) + (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (135560-80-4) → (3S,5S,6R)-3-But-3-enyl-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (135560-82-6)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.833333h;

DOI:10.1021/ja00018a040

Reference yield:

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (135560-80-4) → (3S,5S,6R)-3-[3-((3R,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (135560-79-1,135636-81-6,135636-85-0,135636-86-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 88.5 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.83 h / -78 °C

2: 94 percent / ozone / methanol; CH₂Cl₂ / 0.08 h

3: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 30 min

4: 38 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 3 h / -78 °C

5: 5 percent / AIBN, triphenyltin hydride / toluene / 2.5 h / Heating

With 2,2'-azobis(isobutyronitrile); di-n-butylboryl trifluoromethanesulfonate; triphenylstannane; sodium hexamethyldisilazane; potassium hexamethylsilazane; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja00018a040

upstream raw materials:

4-iodobut-1-ene

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

Downstream raw materials:

(3S,5S,6R)-3-But-3-enyl-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

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

(S,S)-2,6-diaminopimelic acid

(3S,5S,6R)-3-[3-((3R,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester