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

Base Information

• Chemical Name: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• CAS No.: 136707-32-9
• Molecular Formula: C₃₂H₂₉NO₄
• Molecular Weight: 491.587
• Mol file: 136707-32-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 2 articles about (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-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: 84.0%

benzyl bromide (100-39-0) + (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-58-3) → (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136707-32-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ja00024a038

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) → (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136707-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

2: 84 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

With sodium hexamethyldisilazane; potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1021/ja00024a038

Reference yield: 93.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136707-32-9) → (S)-2-amino-2-methyl-3-phenylpropanoic acid (23239-35-2)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 48h; under 2585.7 Torr;

DOI:10.1021/ja00024a038

upstream raw materials:

benzyl bromide

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

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

Downstream raw materials:

(S)-2-amino-2-methyl-3-phenylpropanoic acid